(Dimethyl sulfide)trihydroboron → 2-(2-Chloro-5-(hydroxymethyl)phenyl)ethanol
Reaction equation
CSC.B.[C:5]([CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[Cl:18])[C:12](O)=[O:13])(O)=[O:6]>C1COCC1>[Cl:18][C:17]1[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[CH2:8][CH2:5][OH:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of borane dimethyl sulfide complex (2M in THF, 12.0 mL) was added portionwise over 3 minutes to a suspension of 3-(carboxymethyl)-4-chlorobenzoic acid [Aromatic Intermediate 1, step a] (2.06 g) in dry THF (30 mL) at room temperature. The resulting effervescing dense suspension was stirred at room temperature for 1 hour, then heated to reflux for 1 hour. The cooled mixture was quenched by the portionwise addition of methanol (10 mL) over 2 minutes. The solution was stirred at room temperature for 30 minutes and then concentrated onto silica and purified by flash chromatography on silica eluted with 5% methanol in dichloromethane to afford the subtitled compound as a white solid. Yield 0.983 g.