Methanol → Methyl 4,4,4-trifluoro-3-hydroxybutanoate
Reaction equation
CO.[F:3][C:4]([F:13])([F:12])[C:5](=[O:11])[CH2:6][C:7]([O:9][CH3:10])=[O:8].CC1C=CC(C(C)C)=CC=1>C(N(CC)CC)C.C(O)=O>[F:3][C:4]([F:12])([F:13])[CH:5]([OH:11])[CH2:6][C:7]([O:9][CH3:10])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
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.
Workup
- concentrationfollowed by concentration under reduced pressure
- customan evaporator
- concentrationTo the resulting concentrate
- additionwere added 10 mL of water and 10 mL of ethyl acetate
- additiona saturated sodium carbonate aqueous solution was added
- stirringunder stirring until the pH
- customThe ethyl acetate layer separated from the aqueous layer
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-c40ff7d09a1d4a5aa7e59781bea2eede
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06723871B2
Reaction notes
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