Tetrahydrofuran → (S)-2-methyl-3-phenylpropan-1-ol

Methyl (S)-2-methyl-3-phenylpropionate (5 mmol, 78.4% ee), sodium methoxide (1 mmol), a ruthenium complex 1 (0.01 mmol), and tetrahydrofuran (2 mL) were charged into a 100-mL autoclave equipped with a stirrer. Then, the mixture was subjected to hydrogenation at a hydrogen pressure of 5 MPa at 80° C. for 16 hours. The reaction solution was diluted with 20 mL of diethyl ether, and was passed through 8.9 g of silica gel. The silica gel was washed with diethyl ether. The obtained solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 13.4 g, hexane/ethyl acetate=8/1). (S)-2-Methyl-3-phenylpropanol (657 mg, 1% ee) was obtained.

1. customequipped with a stirrer
2. washThe silica gel was washed with diethyl ether
3. concentrationThe obtained solution was concentrated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (silica gel 13.4 g, hexane/ethyl acetate=8/1)

ORD record

ord-4e4dc67064d244e99b75779e712b5271

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524953B2