Tetrabutylammonium borohydride → (3-o-Tolylbenzo[b]thiophen-2-yl)methanol
Reaction equation
[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([CH3:36])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[S:28][C:29]=1[CH:30]=[O:31]>C1COCC1>[C:19]1([CH3:36])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[S:28][C:29]=1[CH2:30][OH:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Tetrabutylammonium borohydride (nBu4NBH4) (800 mg, 3.10 mmol) was added at RT to a solution of 3-o-tolylbenzo[b]thiophene-2-carbaldehyde (2.07 mmol) in THF (10 mL) and IMS (1 mL) and the mixture was stirred at RT for 1 h. The reaction mixture was then quenched by addition of MeOH and volatiles were removed under reduced pressure. The resulting residues was purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) affording the title compound as an oil (432 mg, 82% over 2 steps). LCMS: RT 3.74 min [M-OH]+ 237.1.