Sodium hydride → t-Butyl 7-phenyl-2-heptenoate

Participants

Reaction Conditions

Reaction Steps

t-butyl diethylphosphonoacetate (18 g; 70 mmol) is dissolved in dry THF (250 mL) and cooled to -40° C. NaH (60% in oil; 2.8 g; 70 mmol) is added and the reaction is warmed to 0° C. Gas evolution is controlled with cooling and then stirred at 20° C. for 30 minutes. 5-Phenylpentanal (11.3 g; 70 mmol) is added and the reaction stirred 20 minutes. The reaction is concentrated to half volume and petroleum ether (500 mL) is added. The reaction is washed with 100 mL water, 100 mL 0.5 N HCl, NaHCO3, brine and dried (MgSO4). The solution is concentrated in vacuo to obtain t-butyl 7-phenylhept-2-enoate which is used directly in Step C.

Provenance & Evidence