Acetic acid, 2-(methylsulfonyl)-, ethyl ester

Colorless to yellow liquid

The synthesis of compound 72 of Formula IScheme 14aO O OMethanesulfonyl-acetic acid (69) (5 3 g, 38 4 mmol) was suspended in ethyl alcohol (5O mL) A 4M solution of HCl in dioxane (8 mL) was added The mixture stirred at reflux for 0 5 h, everything had dissolved at this point The mixture continued to stir at reflux for a total of 16 h Upon cooling, the solution was concentrated in vacuo to approximately 20 mL The oil was diluted with ethyl acetate (300 mL), washed with water (100 mL), brine (100 ml), dried over magnesium sulfate and concentrated in vacuo to a golden oil Purification by flash column chromatography (30percent ethyl acetate in hexanes, Merck silica gel 60, 40-63 μm) afforded the desired product, methanesulfonyl-acetic acid ethyl ester (70) (5 67 g, 34 12 mmol, 89 percent yield), as a To a solution of ethyl 2-bromoacetate (330 g, 1.98 mol) in DMF (1500 mL) was added MeSOGeneral procedure: 34percent H2O2 (2 mL, 20 mmol) was added to a cooled solution ofFeSO4·7H2O (2.78 g, 10 mmol) in DMSO (40 mL), and themixture was stirred for 30 min at 5–10 °C. Then, xanthate 1a(2.4 g, 10 mmol), FeSO4·7H2O (2.78 g, 10 mmol), and H2O2(2 mL, 20 mmol) were added and the reaction mixture was stirred for30 min at 5–10 °C and, then, 2 h at r.t. (TLC control). The reactionmixture was poured into H2O (30 mL) and extracted withEtOAc (4 × 50 mL). The combined organic phases were washedwith brine, dried over anhydrous Na2SO4, filtered, and evaporatedunder reduced pressure. The resulting crude mixture ofproducts was purified by silica column chromatography usingEtOAc–PE (1:4) as eluents. The yield of compound 3a was 1.71 g(86percent).

Molecular Weight:166.20
XLogP3:-0.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:166.02997997
Monoisotopic Mass:166.02997997
Topological Polar Surface Area:68.8
Heavy Atom Count:10
Complexity:198
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes