3-Methoxypropyne → HCID 178495081, compound

Participants

Reaction Steps

A stirred solution of 3-methoxyprop-1-yne (0.207 ml, 2.456 mmol) in THF (2 mL) was treated with BuLi (1.535 ml, 2.456 mmol) dropwise at −78° C. After stirring for 15 min, 13D (300 mg, 0.819 mmol) in THF (2 mL) was added and reaction mixture was warmed to room temperature over 30 min. The reaction was quenched with aq. HOAc and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The residue was purified by Isco silica column (12 g), eluted with ethyl acetate:hexane, 0-70%. Concentration of the appropriate fractions provided 13E (300 mg, 98% yield). This material was taken without characterization to the next step.

Provenance & Evidence