Diisobutylaluminum hydride → HCID 86635037, compound
Reaction equation
CC(C[AlH]CC(C)C)C.C([O:12][C:13]([C@@H:15]1[CH2:19][C:18]([C:20]2[CH:25]=[CH:24][C:23](C)=[CH:22][N:21]=2)=[C:17]([CH3:27])[C@H:16]1[O:28][Si:29]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31])=O)C>C1(C)C=CC=CC=1>[CH3:27][C:17]1[C@@H:16]([O:28][Si:29]([CH2:30][CH3:31])([CH2:34][CH3:35])[CH2:32][CH3:33])[C@H:15]([CH:13]=[O:12])[CH2:19][C:18]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of DIBAL-H (0.44 ml, 1.0 M in hexane, 0.44 mmol, 1.1 equiv) was added dropwise to a solution of silyl ether 29b (150 mg, 0.4 mmol) in toluene (2 ml) at −78° C. The reaction mixture was stirred at that temperature for 1 hr and quenched by dropwise addition of saturated NH4Cl solution (0.2 ml). The reaction mixture was allowed to reach room temperature and a saturated solution of Rochelle salt (1 ml) and brine (0.4 ml) were added. The mixture was extracted with ethyl acetate (3×2 ml) and the combined organic extracts were dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to give crude aldehyde 30b as a yellow liquid which was used in the next step without further purification.