Tert-butyl 6-formyl-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate → Tert-butyl 6-(1-hydroxyethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate
반응식
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][Mg+].[Br-]>C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]([OH:19])[CH3:21])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]참가 물질
4
반응 조건
- 온도
- -78 °C
실험 절차
To a solution of (6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester (Step c, 2.80 g, 10.2 mmol, 1.0 eq) in THF (100 mL) at −78° C. was added a solution of MeMgBr (Aldrich, 1.4 M in toluene/THF (3:1), 29 mL, 40.7 mmol, 4.0 eq) slowly. The reaction was stirred at −78° C. for 20 min, warmed to RT and stirred at RT for 2 h. The reaction was quenched with saturated NaHCO3 (120 mL), and the crude was extracted with EtOAc (100 mL×3). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The title compound was obtained as a white solid. MS (ESI, pos. ion) m/z: 292 (M+1).