Ethyl Acetoacetate → HCID 14851338, compound

Participants

Reaction Conditions

Reaction Steps

To a hexane washed suspension of NaH (1.23 g, 30.7 mmol) in THF (20 mL) at 0° C. under an inert atmosphere, was added a solution of ethyl acetoacetate (3.66 mL, 28.7 mmol) in THF (20 mL). The resulting clear solution was stirred at 0° C. for 15 minutes before n-BuLi (13.1 mL, 28.7 mmol) was added dropwise. This orange solution was stirred at 0° C. for 15 minutes before it was cooled to -78° C. and a solution of the unsaturated aldehyde (7.50 g, 19.2 mmol, Step E) in THF (100 mL) was added dropwise. The reaction was stirred at -78° C. for 1 hour and then it was quenched by adding 4 mL glacial acetic acid and removing the cooling bath. The reaction mixture was partitioned between Et2O and saturated aqueous K2CO3 solution. The organic extracts were dried (MgSO4) and evaporated to give an orange solid. Recrystallization from hexanes gave 8.71 g (87%) of product as a pale yellow orange solid.

Provenance & Evidence