Dichloromethane → Benzyl 3-formyl-2-methylphenylcarbamate

반응식

[C:1]([C:3]1[C:4]([CH3:20])=[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1)#N.CC(C[AlH]CC(C)C)C.ClCCl.[O:33]1CCCC1>>[CH:1]([C:3]1[C:4]([CH3:20])=[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1)=[O:33]

참가 물질

반응물 4

HCID 6344Dichloromethane

HCID 8028Tetrahydrofuran

HCID 14487Diisobutylaluminum hydride

HCID 67994690benzyl N-(3-cyano-2-methylphenyl)carbamate

생성물 1

HCID 86681516Benzyl 3-formyl-2-methylphenylcarbamate수율 87%

반응 조건

온도: -78 °C

실험 절차

To a solution of benzyl 3-cyano-2-methylphenylcarbamate (6.41 g, 24.07 mmol) in tetrahydrofuran (250 mL) at −78° C. was added DIBAL-H in dichloromethane (96 mL, 96 mmol) over 1 hr. The mixture was stirred at −78° C. for 45 min and then at room temperature for 5 hr. It was poured into ice cold water (300 mL) and the resulting mixture was stirred at room temperature for 30 min. The mixture was filtered through CELITE®, and the filtrate was concentrated to remove most of the THF. The remaining aqueous solution was extracted with ethyl acetate (4×150 mL). The combined extract was dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (5.65 g, 20.98 mmol, 87% yield) as a pale yellow solid.