Ethyl Acetoacetate → HCID 14851312, compound

Participants

Reaction Conditions

Reaction Steps

To a hexane washed suspension of NaH (0.90 g, 22.5 mmol) in THF (30 mL) at 0° C. under an inert atmosphere, was added a solution of ethyl acetoacetate (2.69 mL, 21.1 mmol) in THF (30 mL). The resulting clear solution was stirred at 0° C. for 15 minutes before n-BuLi (9.6 mL, 21.1 mmol) was added dropwise. The orange solution was stirred at 0° C. for 15 minutes before it was cooled to -78° C. and a solution of the unsaturated aldehyde (4.73 g, 14.1 mmol, Step E) in THF (80 mL) was added dropwise. This was stirred at -78° C. for 2 hours and then it was quenched by adding ~5 mL HOAc and removing the cooling bath. The reaction was partitioned between Et2O and 5% K2CO3 (aq). The organics were dried (MgSO4) and evaporated to give a yellow oil. Elution from a 4-inch silica column gave 3.17 g (48%) of product as a yellow foam.

Provenance & Evidence