Ethyl 2-oxopentanoate

Light yellow oil liquid

0.1 mol of 2, 2-(dimethylthio)pentanoic acid (11) (19.4 g) was dissolved in 150 ml of toluene and admixed with 2.0 eq of HA solution of 2-oxopentanoic acid (3.00 g, 25.8 mmol), ethanol (1.20 g, 25.8 mmol) andDMAP (0.32 g, 2.6 mmol) in dichloromethane (30 mL) was cooled with an ice bathbefore a solution of DCC (5.86 g, 28.4 mmol) in dichloromethane (15 mL) was addeddropwise during 30 mm. The reaction mixture was stirred for 10 mm at 0°C, then at roomtemperature for 3 h. The precipitate formed during the reaction was filtered on a sintered glass frit and rinsed with dichloromethane (15 mL). The filtrate was concentrated under reduced pressure (40°C) and the residue taken up in diethylether (100 mL). The organic phase was washed with water (3x 30 mL), an aqueous solution of HC1 (10percent, 3x 30 mL), water (30 mL), a saturated aqueous solution of NaHCO3 (3x 30 mL) and water (30 mL). The aqueous phases were re-extracted with diethylether (100 mL). The combined organicphases were dried (Na2SO4) and concentrated under reduced pressure (45°C). Bulb-to- bulb distillation (120°C, 8 mbar) gave 1.80 (45percent) g of a colorless oil.‘H-NMR (500 MHz): ö 4.32 (q, I = 7.2, 2 H), 2.82 (t, I = 7.2, 2 H), 1.67 (hex., I = 7.4, 2 H), 1.37 (t, I = 7.2, 3 H), 0.97 (t, I = 7.5, 3 H).‘3C-NMR (125.8 MHz): ö 194.67 (s), 161.32 (s), 62.35 (t), 41.14 (t), 16.54 (t), 14.03 (q), 13.52 (q).0.1 mol of 2, 2-(dimethylthio)pentanoic acid (11) (19.4 g) was dissolved in 150 ml of toluene and admixed with 2.0 eq of HA solution of 2-oxopentanoic acid (3.00 g, 25.8 mmol), ethanol (1.20 g, 25.8 mmol) andDMAP (0.32 g, 2.6 mmol) in dichloromethane (30 mL) was cooled with an ice bathbefore a solution of DCC (5.86 g, 28.4 mmol) in dichloromethane (15 mL) was addeddropwise during 30 mm. The reaction mixture was stirred for 10 mm at 0°C, then at roomtemperature for 3 h. The precipitate formed during the reaction was filtered on a sintered glass frit and rinsed with dichloromethane (15 mL). The filtrate was concentrated under reduced pressure (40°C) and the residue taken up in diethylether (100 mL). The organic phase was washed with water (3x 30 mL), an aqueous solution of HC1 (10percent, 3x 30 mL), water (30 mL), a saturated aqueous solution of NaHCO3 (3x 30 mL) and water (30 mL). The aqueous phases were re-extracted with diethylether (100 mL). The combined organicphases were dried (Na2SO4) and concentrated under reduced pressure (45°C). Bulb-to- bulb distillation (120°C, 8 mbar) gave 1.80 (45percent) g of a colorless oil.‘H-NMR (500 MHz): ö 4.32 (q, I = 7.2, 2 H), 2.82 (t, I = 7.2, 2 H), 1.67 (hex., I = 7.4, 2 H), 1.37 (t, I = 7.2, 3 H), 0.97 (t, I = 7.5, 3 H).‘3C-NMR (125.8 MHz): ö 194.67 (s), 161.32 (s), 62.35 (t), 41.14 (t), 16.54 (t), 14.03 (q), 13.52 (q).

Molecular Weight:144.17
XLogP3:1.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:144.078644241
Monoisotopic Mass:144.078644241
Topological Polar Surface Area:43.4
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes