Benzyl Alcohol → 3-(Benzyloxy)propane-1,2-diol
Reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5].[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F-].[Cs+]>>[CH2:6]([O:13][CH2:1][C@@H:2]([OH:3])[CH2:4][OH:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
4
Conditions
- Temperature
- 120 °C
Procedure
A mixture of (S)-glycidol (77) (20 g, 0.27 mol), benzyl alcohol (27.9 mL, 0.27 mol) and CsF (0.82 g, 5.40 mmol) was heated with stirring at 120° C. for 16 h. Unreacted benzyl alcohol was removed using a rotary evaporator attached to a high vacuum line. The product was partitioned between EtOAc and water, and the organic extract was evaporated and chromatographed on silica. Elution with petroleum ether gave fore fractions, and then further elution with EtOAc/petroleum ether (3:7) gave (2S)-3-(benzyloxy)-1,2-propanediol (78) (9.52 g, 19%) as a viscous oil: [α]19 −3.64° (c, 6.59, CHCl3); 1H NMR (CDCl3) δ 7.38-7.28 (m, 5H), 4.56 (s, 2H), 3.92-3.87 (m, 1H), 3.71 (dd, J=11.4, 3.9 Hz, 1H), 3.64 (dd, J=11.4, 5.4 Hz, 1H), 3.61-3.57 (m, 2H), 2.60 (br, 1H), 2.22 (br, 1H). APCI MS m/z 183 [M+H]+.