P-Cymene → Isopropyl 4,4,4-trifluoro-3-hydroxybutyrate
Reaction equation
O1CCCC1.CC1C=CC(C(C)C)=CC=1.[F:16][C:17]([F:28])([F:27])[C:18](=[O:26])[CH2:19][C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21]>C(N(CC)CC)C.C(O)=O>[F:16][C:17]([F:27])([F:28])[CH:18]([OH:26])[CH2:19][C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
Into 6 mL of tetrahydrofuran were dissolved 6.4 mg of RuCl[(1R,2R)-p-TsNHCH(C6H5)CH(C6H5)NH2] (p-cymene), 5 mL of a mixture of formic acid-triethylamine (5:2 in molar ratio), 1.0 g of isopropyl 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 isopropyl 4,4,4-trifluoro-3-hydroxybutanoate. Upon the measurement under the above conditions, the optical purity and conversion were found to be 96.2% 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-4c093569b77e429f924c6b12716ffc7c
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06723871B2
Reaction notes
Loading…