반응 #60392

반응 방정식

(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester

MeMgBr

→

title compound

[6-(1-hydroxy-ethyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-carbamic acid tert-butyl Ester

용매

THF

반응 조건

후처리

1. 1
   온도warmed to RT
2. 2
   workup.STIRRINGstirred at RT for 2 h
3. 3
   기타The reaction was quenched with saturated NaHCO3 (120 mL)
4. 4
   추출the crude was extracted with EtOAc (100 mL×3)
5. 5
   세척The extract phase was washed with saturated NaCl
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated

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).

출처