Diethyl Ether → Methyl [2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1h-indol-3-yl](oxo)acetate

Participants

Reaction Conditions

Reaction Steps

2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indole (1 eq) was dissolved in ether (0.38M) and the solution was cooled to 0° C. Oxalyl chloride (2M in CH2Cl2) (1.2 eq) was added to the above cold solution with vigorous stirring. Precipitation occurred. The suspension was kept stirred at 0° C. for 30 minutes. Then MeOH (3/5 volume of oxalyl chloride solution) was added to the reaction mixture, followed by NEt3 (6/5 volume of oxalyl chloride solution). The resulting mixture was then diluted with MeOH (6/5 volume of oxalyl chloride solution) before it was poured into water (4× volume of oxalyl chloride solution). Extract with EtOAc. Organic phase washed with brine, dried over Na2SO4, and concentrated to give methyl [2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl](oxo)acetate (brown solid) in 65% yield.

Provenance & Evidence