Sodium hydride → (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid benzyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[H-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (8.1 g, 34 mmol) was dissolved in benzylic alcohol (14.7 g, 135 mmol) and freshly washed sodium hydride (1.63 g, 41 mmol) was caustiosuly added under nitrogen atmosphere. The resulting mixture was warmed up to 50° C. under vacuum and after 6 h toluene was added and the mixture was extracted with aq. KHSO4 (2N). The combined organic layers were dried and evaporated under high vacuum at 70° C. to afford title compound as an oil (9.51 g, 93.1%). 1H NMR (400 MHz, CDCl3): δ 7.19-7.40 (m, 5H), 7.03-7.06 (d, 2H), 6.68-6.71 (d, 2H), 5.14 (s, 2H), 4.03-4.06 (t, 1H), 3.57-3.61 (m, 1H), 3.36-3.40 (m, 1H), 2.97 (s, 1H), 1.14-1.18 (t, 3H).