Ethanol sodium ethoxide → (2S,3R)-3-benzyl-2-oxiranecarboxylic acid
Reaction equation
Cl[CH:2]([C@H:8]([OH:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].[O-]CC.[Na+].C(O)C>C(O)C>[CH2:9]([C@H:8]1[O:16][C@@H:2]1[C:3]([OH:5])=[O:4])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl (3R)-2-chloro-3-hydroxy-4-phenylbutyrate (122 mg, 0.5 mmol) was dissolved in ethanol (3 ml), and 20 wt % sodium ethoxide/ethanol solution (254 mg) was gradually added. The mixture was stirred at room temperature for 3 hours, and the solvent was evaporated away under reduced pressure. Water (5 ml) was added, and the pH was adjusted to 13 with 30 wt % aqueous solution of sodium hydroxide. The mixture was washed with toluene (5 ml), and the pH was adjusted to 1.5 with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate (15 ml), and drying was carried out with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain the title compound as a brown oil (66 mg, yield: 74%).