Triphenylphosphine → HCID 68686090, compound

Participants

Reaction Steps

1.3 mL of ethyl ethynyl ether (50% v/v hexane solution) was dissolved in 10 mL of tetrahydrofuran, and in an ice bath, 2.04 mL of borane-tetrahydrofuran complex (1.0M tetrahydrofuran solution) was added dropwise over 30 minutes. Thereafter, the reaction mixture was heated to room temperature, and stirred for 3 hours. Thereto, 10 mL of tetrahydrofuran solution containing 330 mg of the 4-iodo-N-[(1S)-1-phenylethyl]-2-pyridinamine [58-1], 11.5 mg of palladium acetate, 40.2 mg of triphenylphosphine, and 1.28 mL of a 4N aqueous solution of sodium hydroxide, were added, and further stirred at room temperature for 5 hours. The reaction mixture was diluted with 150 mL of ethyl acetate, washed with water and saturated brine in the subsequent order, and the thus 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 94 mg of 4-[(E)-2-ethoxyethenyl]-N-[(1S)-1-phenylethyl]-2-pyridinamine [58-2] as a brown oily product.

Provenance & Evidence