Sodium hydride → Ethyl trans-3, 5-di-t-butylcinnamate

Participants

Reaction Conditions

Reaction Steps

A solution of 0.3 g of the aldehyde prepared above in THF (1 mL) was added to a solution of sodium triethylphosphonoacetate prepared by combining triethylphosphonoacetate (0.37 g, 1.2 eq.) and NaH (0.1 g, 50% dispersion, 1.5 eq.) in THF (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour and then quenched with saturated ammonium chloride and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate and evaporated to give ethyl trans-3, 5-di-t-butylcinnamate as a yellow oil used directly for the next step.

Provenance & Evidence