Diisopropyl Ether → (R)-2-bromo-1-(3-chlorophenyl)ethanol

To 100 mg (0.4 mmol) of 2-bromo-1-(3-chlorophenyl)ethanol were added 30 mg of Lipase QL (available from Meito Sangyo Co., Ltd.) and 40 mg (0.4 mmol) of acetic anhydride. Diisopropyl ether was added to the mixture to make the total volume to 1 ml. The reaction mixture was then allowed to undergo reaction at a temperature of 35° C. for 72 hours. After the termination of the reaction, the enzyme was removed by filtration. The resulting filtrate was then concentrated under reduced pressure. The concentrated solution was analyzed by 1H-NMR. As a result, it was found that (R)-2-bromo-1-(3-chlorophenyl) ethanol and (S)-2-bromo-1-(3-chlorophenyl)ethyl acetate had been produced in a proportion of 2:3. The concentrated solution was then separated by a thin layer silica gel chromatography. As a result, (R)-2-bromo-1-(3-chlorophenyl)ethanol ([α]D20 =-25.6°, C=1.05) and (S)-2-bromo-1-(3-chlorophenyl)ethyl acetate ([α]D20 =+40.4°, C=0.60) were obtained. The optical purity of (R)-2-bromo-1-(3-chlorophenyl)ethanol thus obtained was analyzed by Chiral HPLC. The results were 100% ee.

1. customreaction at a temperature of 35° C. for 72 hours
2. customAfter the termination of the reaction
3. customthe enzyme was removed by filtration
4. concentrationThe resulting filtrate was then concentrated under reduced pressure
5. customhad been produced in a proportion of 2:3
6. customThe concentrated solution was then separated by a thin layer silica gel chromatography

ORDレコード

ord-f640bfcaaa3b458781a31bff37f1c3b1

出典データセット

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05841001