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

Methyl (S)-2-methyl-3-phenylpropionate (5 mmol, 78.4% ee), a dichlororuthenium complex 8 (0.05 mmol), sodium methoxide (5 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 solution thus obtained was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 13.4 g, hexane/ethyl acetate=8/1). Thus, (S)-2-methyl-3-phenylpropanol (645 mg, 18.4% ee) was obtained.

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

ORD record

ord-7c6031965b714b44b0f44898197ae636

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524953B2