Tetrahydrofuran → (S)-2-{2[2-(1-methoxycarbonylethoxy)phenyl]vinyl}-1-methylindole

Participants

Reaction Steps

To a solution of 1.50 g (6.02 mmol) of 2-[2-(2-hydroxyphenyl)vinyl]-1-methylindole, 1.89 g (7.21 mmol) of triphenylphosphine and 0.69 ml (7.22 mmol) of R-(+)-methyl lactate in 15 ml of THF was added 1.14 ml (7.24 mmol) of diethylazodicarboxylate under an ice-cooled condition, followed by stirring at room temperature for 2 hours. Brine was added to the reaction mixture, followed by extraction with methylene chloride. The extract was dried over Na2SO4, and evaporated. CHCl3 -n-hexane was added to the residue and, after filtration, the organic layer was purified by silica gel column chromatography (CHCl3 /n-hexane/AcOEt=10/10/1) to give 1.82 g (90%) of (S)-2-{2[2-(1-methoxycarbonylethoxy)phenyl]vinyl}-1-methylindole.

Provenance & Evidence