tert-Butyl (triphenylphosphoranylidene) acetate → HCID 58105211, compound

Participants

Reaction Steps

6-Hydroxymethylpyridine-2-carbaldehyde (15.3 g) was dissolved in 250 mL of dry DMF, and 50 g of (t-butoxycarbonylmethylene)triphenylphosphorane was added to the above solution, and then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was thrown into ice-water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added 300 mL of a mixture of hexane-ethyl acetate (2:1), the insoluble portion was filtrated off. The filtrate was concentrated under reduced pressure, the residue was purified by chromatography on silica gel (hexane-ethyl acetate=2:1) to give 16.86 g of t-butyl 3-(6-hydroxymethylpyridin-2-yl)-trans-acrylate and 5.69 g of t-butyl 3-(6-hydroxymethylpyridin-2-yl)-cis-acrylate.

Provenance & Evidence