Pivaloylacetonitrile

white to cream crystals or crystalline powder

NaH (50 percent in paraffin oil) (1.2 eq., 4.6 g) was dissolved in 1 , 4-dioxane (120 ml) and the mixture was stirred for a few minutes. Acetonitrile (1.2 eq., 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-I) (1 eq., 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 ml). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from hexane (100 ml) 5 g of the product (J-Il) (51 percent yield) was able to be obtained as a solid brown substance.NaH (50 percent in paraffin oil) (1.2 eq., 4.6 g) was dissolved in 1 , 4-dioxane (120 ml) and the mixture was stirred for a few minutes. Acetonitrile (1.2 eq., 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-I) (1 eq., 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 ml). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from hexane (100 ml) 5 g of the product (J-Il) (51 percent yield) was able to be obtained as a solid brown substance.NaH (50percent in paraffin oil) (1.2 equiv., 4.6 g) was dissolved in 1, 4-dioxane (120 mL) and stirred for a few minutes. Acetonitrile (1.2 equiv., 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-I) (1 equiv., 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete conversion the reaction mixture was poured into iced water (200 g), acidified to pH 4.5, and extracted with dichloromethane (12.x.250 mL). The combined organic phases were dried over sodium sulphate, distilled, and after recrystallisation from hexane (100 mL) 5 g of the product (J-II) (51percent yield) was obtained as a brown solid substance.Step j02: NaH (50percent in paraffin oil) (1.2 eq., 4.6 g) was dissolved in 1, 4-dioxane (120 ml) and the mixture was stirred for a few minutes. Acetonitrile (1.2 eq., 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-I) (1 eq., 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12.x.250 ml). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from hexane (100 ml) 5 g of the product (J-II) (51percent yield) was able to be obtained as a solid brown substance.NaH (50 percent in paraffin oil) (1.2 eq., 4.6 g) was dissolved in 1 , 4-dioxane (120 ml) and the mixture was stirred for a few minutes. Acetonitrile (1.2 eq., 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-l) (1 eq., 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 ml). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from hexane (100 ml) 5 g of the product (J-ll) (51 percent yield) was able to be obtained as a solid brown substanceStep j02: NaH (50percent in paraffin oil) (1.2 eq., 4.6 g) was dissolved in 1, 4-dioxane (120 ml) and the mixture was stirred for a few minutes. Acetonitrile (1.2 eq., 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-I) (1 eq., 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12.x.250 ml). The combined organic phases were dried over sodium sulfate, distilled and after recrystallisation from hexane (100 ml) 5 g of the product (J-II) (51percent yield) was able to be obtained as a solid brown substance.NaH (50 percent in paraffin oil) (1.2 equivalents, 4.6 g) was dissolved in 1 , 4-dioxane (120 mL) and the mixture was stirred for a few minutes. Acetonitrile (1.2 equivalents, 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-l) (1 equivalents, 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 mL). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from n-hexane (100 mL) 5 g of the product (J-ll) (51 percent yield) was able to be obtained as a solid brown substance.Step j02 NaH (50 percent in paraffin oil) (1 .2 equivalents, 4.6 g) was dissolved in 1 , 4-dioxane (120 mL) and the mixture was stirred for a few minutes. Acetonitrile (1 .2 equivalents, 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-l) (1 equivalents, 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 mL). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from n-hexane (100 mL) 5 g of the product (J-ll) (51 percent yield) was able to be obtained as a solid brown substance.Step j02: NaH (50 percent in paraffin oil) (1 .2 equivalents, 4.6 g) was dissolved in 1 , 4-dioxane (120 mL) and the mixture was stirred for a few minutes. Acetonitrile (1 .2 equivalents, 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-l) (1 equivalents, 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 mL). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from n-hexane (100 mL) 5 g of the product (J-ll) (51 percent yield) was able to be obtained as a solid brown substance.Step j02: NaH (50 percent in paraffin oil) (1 .2 equivalents, 4.6 g) was dissolved in 1 , 4-dioxane (120 mL) and the mixture was stirred for a few minutes. Acetonitrile (1 .2 equivalents, 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-l) (1 equivalents, 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 mL). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from n-hexane (100 mL) 5 g of the product (J-ll) (51 percent yield) was able to be obtained as a solid brown substance.NaH (50 percent in paraffin oil) (1 .2 equivalents, 4.6 g) was dissolved in 1 , 4-dioxane (120 mL) and the mixture was stirred for a few minutes. Acetonitrile (1 .2 equivalents, 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-l) (1 equivalents, 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 mL). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from n-hexane (100 mL) 5 g of the product (J-ll) (51 percent yield) was able to be obtained as a solid brown substanceStep j02: NaH (50 percent in paraffin oil) (1 .2 equivalents, 4.6 g) was dissolved in 1 , 4-dioxane (120 mL) and the mixture was stirred for a few minutes. Acetonitrile (1 .2 equivalents, 4.2 g) was added dropwise within 15 min and the mixture was stirred for a further 30 min. The methyl pivalate (J-l) (1 equivalents, 10 g) was added dropwise within 15 min and the reaction mixture was refluxed for 3 h. After complete reaction, the reaction mixture was placed in iced water (200 g), acidified to pH 4.5 and extracted with dichloromethane (12 x 250 mL). The combined organic phases were dried over sodium sulphate, distilled and after recrystallisation from n-hexane (100 mL) 5 g of the product (J-ll) (51 percent yield) was able to be obtained as a solid brown substance.

Molecular Weight:125.17
XLogP3:1.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:125.084063974
Monoisotopic Mass:125.084063974
Topological Polar Surface Area:40.9
Heavy Atom Count:9
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes