Isopropanol → Ethyl 4,4,4-trifluoro-3-hydroxybutanoate

Temperature

35 °C

To 10 mL of i-propanol 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 94.8% e.e. and 99.9%, respectively.

1. concentrationfollowed by concentration under reduced pressure
2. customan evaporator
3. concentrationTo the resulting concentrate
4. additionwere added 10 mL of water and 10 mL of ethyl acetate
5. additiona saturated sodium carbonate aqueous solution was added
6. stirringunder stirring until the pH
7. customThe ethyl acetate layer separated from the aqueous layer
8. concentrationwas concentrated

ORD record

ord-ecedbf72577f48b59179e742560dcb3e

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723871B2