Methanol → HCID 69270322, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 5-[3-(tert-butyldimethyl-silyloxy)propoxy]-1-isopropyl-1H-indole (0.43 g, 1.124 mmol) in tetrahydrofuran (40 mL). Add 2,6-lutidine (0.43 mL, 3 eq) and cool to 0° C. Add oxalyl chloride dropwise and stir for 1.5 hours then cool to −78° C., add methanol (0.1 mL, 2 eq) and treated with sodium methoxide (25% w/w in methanol, 22.5 mL). Stir for 1 hour then dilute with ethyl acetate and extract with saturated sodium bicarbanate then brine. Dry over magnesium sulfate, filter and concentrate. Purification by column chromatography (4:1 hexanes:ethyl acetate) affords the title compound as a light yellow oil. MS (ES, m/z): 434.3 (M+1).

Provenance & Evidence