Dimethylformamide → HCID 22490925、化合物

反応式

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7][CH:6]=[C:5]2[C:17]([CH3:20])([CH3:19])[CH3:18].C([Li])CCC.CN(C)[CH:28]=[O:29]>CCOCC>[C:17]([C:5]1[C:4]2[CH:3]=[C:2]([CH:28]=[O:29])[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:9]=2[C:8]([CH3:16])([CH3:15])[CH2:7][CH:6]=1)([CH3:20])([CH3:19])[CH3:18]

参加物

反応条件

温度: -40 °C

実験手順

To a solution of 6-bromo-4-tert-butyl-7-ethoxy-1,1-dimethyl-1,2-dihydronaphthalene (Compound A-6, 600 mg, 1.78 mmol) in ether (10 mL) at −78° C. was added n-butyllithium (2.3 mL 1.6 M in hexane, 3.9 mmol). After stirring at −78° C. for 25 nm, N,N-dimethylformamide (2 mL) was added and the reaction mixture was allowed to warm to −40° C. over 10 min. The reaction mixture was quenched with water and extracted with ether. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 3% to 10% ethyl acetate in hexane) afforded the title compound as a white solid.