Methanol → Methyl 4,4,4-trifluoro-3-hydroxybutanoate

Participants

Reaction Conditions

Reaction Steps

To 6 mL of methanol were added 5 mL of a mixture of formic acid-triethylamine (5:2 in molar ratio), 1.0 g of methyl 4,4,4-trifluoro-3-oxobutanoate, and 7.5 mg of RuCl[(1R,2R)-p-TsNHCH(C6H5)CH(C6H5)NH2] (p-cymene), and the whole was stirred at 35° C. for 15 hours, followed by concentration under reduced pressure using an evaporator. To the resulting concentrate were added 10 mL of water and 10 mL of ethyl acetate, and then a saturated sodium carbonate aqueous solution was added thereto under stirring until the pH became 7 or higher. The ethyl acetate layer separated from the aqueous layer was concentrated to obtain optically active methyl 4,4,4-trifluoro-3-hydroxybutanoate. Upon the measurement under the above conditions, the optical purity and conversion were found to be 94.6% e.e. and 100%, respectively.

Provenance & Evidence