Triphenylphosphine → HCID 18506912, compound

Participants

Reaction Steps

50 g of ethyl ethynyl ether (50% v/v hexane solution) was dissolved in 200 mL of tetrahydrofuran, 119 mL of borane-tetrahydrofuran complex (1.0M tetrahydrofuran solution) was added dropwise over 30 minutes under an ice-cold condition, then the reaction mixture was heated to room temperature, and further stirred for 4 hours. Thereto, 100 mL of tetrahydrofuran solution containing 19.1 g of 4-chloro-2-methylthiopyrimidine, 1.87 g of palladium acetate, 2.18 g of triphenylphosphine, and 159 mL of a 3N aqueous solution of sodium hydroxide were added, and was further stirred overnight at room temperature. Under reduced pressure, the tetrahydrofuran was distilled off, water was added to the residue, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 9.7 g of 4-[(E)-2-ethoxyvinyl]-2-(methylthio)pyrimidine [25-2] as a brown oily product.

Provenance & Evidence