Methanol → HCID 13271044, compound

Participants

Reaction Conditions

Reaction Steps

5-((E)-2-Methoxycarbonyl-vinyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.200 g, 0.573 mmol, 1 eq) was suspended in dry THF (10 mL) under Ar. Methanol (0.116 mL, 2.87 mmol, 5.0 eq) was added followed by cooling to 4° C. and the addition of lithium borohydride (1.40 mL of 2 M, 2.87 mmol, 5.0 eq). The reaction mixture was stirred and allowed to warm to room temperature, then heated to reflux. The reaction was followed by TLC (CH2Cl2/MeOH 9/1). After 24 hours, the reaction was quenched with brine and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with CH2Cl2/MeOH 9/1. 0.149 g (81% yield) of the indole-propanol was obtained as a white solid, with some contamination by the E-allylic alcohol (20%-30%).

Provenance & Evidence