Diisobutylaluminum hydride → HCID 39232332, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([C:15](N(OC)C)=[O:16])[CH:9]=2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([CH:15]=[O:16])[CH:9]=2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
4′,6-Dichloro-N-methoxy-N-methylbiphenyl-3-carboxamide (1.0 g, 3.2 mmol, 1.0 eq) was dissolved in dry THF and stirred for 10 minutes. The solution was cooled to −78° C. and DIBAL-H (1 M solution, 1.83 g, 12.9 mmol, 4 eq, 13 mL) was slowly added over 15-30 minutes. The reaction mixture was stirred for 1 h at −78° C., quenched with saturated NH4Cl solution at −78° C. and stirred for 30 minutes at ambient temperature. Water and ethyl acetate were added into the reaction mixture. The aqueous layer was separated and extracted twice with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum to give the desired product (0.7 g, 87%). 1H NMR (400 MHz, CDCl3) δ 7.06-7.09 (d, 2H), 7.24-7.27 (d, 2H), 7.40 (s, 1H), 7.55-7.58 (d, 1H), 7.90-7.95 (m, 1H).