Acetone → 1-(2-Chlorophenyl)butane-1,3-dione

Participants

Reaction Conditions

Reaction Steps

A 2.5 M hexane solution of BuLi (16.46 mL, 41.1 mmol) was added dropwise to a solution of diisopropylamine (6.11 mL, 42.9 mmol) in THF (150 mL) at −78° C. The mixture was stirred at 0° C. for 15 min and cooled to −78° C. Acetone (3.02 mL, 41.1 mmol) was added dropwise. After 2 h at −78° C., 2-chlorobenzoyl chloride (3.00 g, 17.14 mmol) in THF (10 mL) was added dropwise. The flask was rinsed with THF (2 mL) and added. After 1 h at −78° C., the mixture was quenched with brine (200 mL) and acidified to pH ˜1 with 1 N HCl. The organic solvents were evaporated in vacuo. The aqueous residue was extracted with EtOAc (3×100 mL). The combined extracts were dried (MgSO4) and concentrated to give crude 1-(2-chlorophenyl)butane-1,3-dione as a yellow liquid. The crude material was taken to next step without purification. MS (ES+) m/z: 197 (M+H).

Provenance & Evidence