Sodium borohydride → Methyl 3-(1-Hydroxyethyl)benzoate

General Procedure EE: Into the EtOH (70 ml) solution of methyl-3-acetylbenzoate (771 mg, 3.98 mmol) was added sodium borohydride (232 mg, 6.09 mmol). The mixture was stirred at rt under an atmosphere of nitrogen for one hour. After that time, the mixture was quenched with saturated NH4Cl followed by water, extracted with EtOAc (3×50 ml). The extracts were washed with water (50 ml), brine (50 ml), dried over MgSO4. After concentrated in vacuo, a beige oil (6269-42, 700 mg) was obtained. It was purified by chromatography on silica gel (25 g) eluting with 20% (200 ml), 30% (200 ml) and 40% EtOAc/hexane (200 ml) to give the title compound as a colorless oil (504 mg, 67% yield). TLC: Rf=0.41 (eluting with 30% EtOAc/hexane). 1H NMR (400 MHz, CDCl3): δ=1.52 (d, J=6.4 Hz, 3H), 1.89 (d, J=4.0 Hz, 1H), 3.92 (s, 3H), 4.93-5.01 (m, 1H), 7.43 (t, J=8.0 Hz, 1H), 7.59 (md, J=8.0 Hz, 1H), 7.95 (td, J=1.6 & 8.0 Hz, 1H), 8.03-8.05 (m, 1H). MS (ES+): m/z 181.19 [MH+]. HPLC: tR=2.51 min (polar—5 min, ZQ3).

1. customAfter that time, the mixture was quenched with saturated NH4Cl
2. extractionextracted with EtOAc (3×50 ml)
3. washThe extracts were washed with water (50 ml), brine (50 ml)
4. dry with materialdried over MgSO4
5. concentrationAfter concentrated in vacuo
6. customa beige oil (6269-42, 700 mg) was obtained
7. customIt was purified by chromatography on silica gel (25 g)
8. washeluting with 20% (200 ml), 30% (200 ml) and 40% EtOAc/hexane (200 ml)

ORD record

ord-2ad6df53f6964e7cb49e3064ae458806

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2