C(#N)C.[CH3:4][C:5]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18])([CH3:14])[CH2:6][C@:7]1([C:10]([F:13])([F:12])[F:11])[CH2:9][O:8]1.Cl([O-])=[O:24].[Na+].S(=O)(=O)(O)N>[Cl-].[Na+].O>[CH3:14][C:5]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]([OH:24])=[O:18])([CH3:4])[CH2:6][C@:7]1([C:10]([F:12])([F:13])[F:11])[CH2:9][O:8]1
To a stirred, ice-cooled, acetonitrile (250 mL) solution of 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzaldehyde (20 g, 73.5 mmol) was added a solution of sodium chlorite (7.4 g, 73.5 mmol in 100 mL water) followed immediately by a solution of sulfamic acid (7.13 g, 73.5 mmol in 100 mL water). After 30 minutes, the ice-cooled reaction mixture was treated with 500 mL of brine and extracted with three 300 mL portions of ethyl acetate. The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo to give 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzoic acid as a colorless thick oil (18 g, 85%).
Loading…
