Dimethyl Sulfide → 2-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethanol

Participants

Reaction Steps

Methyl [1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy }methyl)-5-chloro-1H-indol-3-yl](oxo)acetate (1 eq) was dissolved in THF (0.46M), then BH3.Me2S (2M in THF) (2 eq) was added to it. The resulting mixture was refluxed with stirring overnight under N2. The reaction mixture was cooled to rt, then quenched slowly with 1N NaOH(aq). Followed by regular work-up (eg. EtOAc extraction, brine wash, etc.). Removed the solvent and purified using a column with CH2Cl2 as eluent to give 2-[1-benzhydryl-2-({[tert-butyl(dimethyl)silyl]oxy }methyl)-5-chloro-1H-indol-3-yl]ethanol (yellow solid) in 72% yield.

Provenance & Evidence