Tetrahydrofuran → 2-(3-Chlorophenyl)-2-methylpropanal

반응식

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:5]=[CH:6][CH:7]=1.CC(C[AlH]CC(C)C)C.C1C[O:25]CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:25])[CH:5]=[CH:6][CH:7]=1

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 14487Diisobutylaluminum hydride

HCID 213298602-(3-Chlorophenyl)-2-methylpropanenitrile

생성물 1

HCID 820751242-(3-Chlorophenyl)-2-methylpropanal수율 88%

반응 조건

온도: -78 °C

실험 절차

To a solution of 2-(3-chlorophenyl)-2-methylpropanenitrile (5.3 g, 29.2 mmol) in THF (80 mL, anhyd) at −78° C. was added dropwise DIBAL-H (1M in toluene, 87 mL, 87 mmol, 3 eq) over 2 h. After stirring 30 min at −78° C., the reaction mixture was allowed to warm to room temperature, quenched with 2N HCl and extracted with EtOAc. The combined extracts were dried over MgSO4 and evaporated in vacuo to give 2-(3-chlorophenyl)-2-methylpropanal (4.6 g, 88%). 1H NMR (400 MHz, CDCl3) δ 9.48 (s, 1H), 7.32 (m, 3H), 7.14 (m, 1H), 1.51 (s, 6H).