Sodium Hydroxide → HCID 21272035, compound

Participants

Reaction Steps

A mixture of methyl 1-ethyl-1,3,4,9-tetrahydro-8-hydroxy-pyrano[3,4-b]indole-1-acetate (6 g, 20.8 mmol), 3-bromo-1-trimethylsilyl-1-propyne [4.8 g, 25 mmol, prepared according to R. B. Miller, Synth. Comm., 2, 267 (1972)] and 2.5N--NaOH (10 mL, 25 mmol) in DMSO (60 mL) was heated under nitrogen for 30 minutes at 120° C. Upon cooling, the micture was diluted with 2 volumes of water, acidified with 2N--KHSO4 solution and extracted with ether. The extracts were dried (Na2SO4) and concentrated in vacuo. The residual oil (7 g) was flash-chromatographed (silica Merck-60, chloroform) to provide methyl 1-ethyl-1,3,4,9-tetrahydro-8-[(2-propynyl)oxy]-pyrano[3,4-b]indole-1-acetate (5.6 g, 83%) as an oil.

Provenance & Evidence