3-Chloropropiophenone → (S)-(-)-3-Chloro-1-phenyl-1-propanol

A solution of 3-chloropropiophenone (8.93 g, 50 mmol in 25 ml THF) was added to (-) diisopinocampheylchloroborane (Ipc2BCl, 18.0 g, 56 mmole, in 25 ml THF at -24° C.). The reaction was complete within 7 hours after which all volatiles were removed under reduced pressure. The residue was dissolved in ether, and diethanolmine (2 equivalents) was added. The resulting suspension was stirred for two hours and filtered. The solid residue was washed with ether and the combined washings and filtrate were concentrated. Distillation furnished[S]-(-)-1-chloro-3-phenyl-3-propanol. Yield: 6.1g, 72%; mp 56°-57° C.; D23-25.25, c=7.05, CHCl3 ; 97% ee.

1. customafter which all volatiles were removed under reduced pressure
2. dissolutionThe residue was dissolved in ether
3. additiondiethanolmine (2 equivalents) was added
4. filtrationfiltered
5. washThe solid residue was washed with ether
6. concentrationthe combined washings and filtrate were concentrated
7. distillationDistillation furnished[S]-(-)-1-chloro-3-phenyl-3-propanol

ORD record

ord-e6969f18b2a64fb79a2408a24969e51c

Source dataset

uspto-grants-1990_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04918246