Acetonitrile → Ethyl 4,4,4-trifluoro-3-hydroxybutanoate
Reaction equation
C(#N)C.CC1C=CC(C(C)C)=CC=1.[F:14][C:15]([F:25])([F:24])[C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(N(CC)CC)C.C(O)=O>[F:14][C:15]([F:24])([F:25])[CH:16]([OH:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
To 10 mL of acetonitrile were added 5 mL of a mixture of formic acid-triethylamine (5:2 in molar ratio), 7 mg of RuCl[(1R,2R)-p-TsNHCH(C6H5)CH(C6H5)NH2] (p-cymene), and 1.0 g of ethyl 4,4,4-trifluoro-3-oxobutanoate, 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 ethyl 4,4,4-trifluoro-3-hydroxybutanoate. Upon the measurement under the above conditions, the optical purity and conversion were found to be 95.0% e.e. and 99.9%, 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-7f40b0feb4fe4523a5609b0fb6dfb186
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06723871B2
Reaction notes
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