Triphenylphosphine → HCID 86619139, compound

Participants

Reaction Steps

2 g of ethyl ethynyl ether (50% v/v hexane solution) was dissolved in 20 mL of tetrahydrofuran, and 4.7 mL of borane-tetrahydrofuran complex (1.0M tetrahydrofuran solution) was added under an ice-cold condition. After stirring the mixture at room temperature for 3 hours, 50 mL of tetrahydrofuran, 3 g of 2,6-dichloro-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine [56-1], 222 mg of triphenylphosphine, 63 mg of palladium acetate, and 7.0 mL of 4N aqueous solution of sodium hydroxide were added, and the mixture was heated overnight under reflux. The reaction mixture was cooled back to room temperature, diluted with ethyl acetate, and then washed with water and saturated saline in the subsequent order. The obtained organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 676 mg of 2-chloro-6-[(E)-2-ethoxyvinyl]-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine [56-2] as a light brown oily product.

Provenance & Evidence