Tetrahydrofuran → 2-(3-Chlorophenyl)-2-methylpropanal
Reaction equation
[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]=1Participants
4
Conditions
- Temperature
- -78 °C
Procedure
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).