Sodium hydride → HCID 54348092, compound

Participants

Reaction Steps

To a slurry of NaH (1.1 g, 27.5 mmol) in 80 mL of THF at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (4.42 g, 24.9 mmol) in 20 mL of THF. The mixture was stirred for 30 min, and a solution of 3-cyclopentoxy-4-methoxybenzaldehyde (5.0 g, 22.7 mmol) in 20 mL of THF was then added dropwise. The mixture was for 2 hr and then diluted with ether. The mixture was washed with 1M H3PO4, H2O, and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to yield 3-cyclopentoxy-4-methoxycinnamonitrile (4.8 g, 87%) as a yellow oil, which was carried on without further purification. 1H-NMR (300 MHz): δ 3.89 (s, 3), 5.69 (d, 1, J=16.6).

Provenance & Evidence