Acetyl chloride → Acetoacetic Acid

Participants

Reaction Steps

Reflux dl-13-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one (1.0 g) for one and one-half hours with acetic anhydride (16 cc), acetyl chloride (8.0 cc) and pyridine (0.8 cc). Remove the liquids under reduced pressure and partition the dry crystalline residue between benzene-ether and water. Wash the organic solvents under reduced pressure and triturate the residue with ice-cold ether to provide dl-13-ethyl-17α-ethynyl-3,17-dihydroxygona-3,5-diene, diacetate (0.725 g) m.p. 144°-150°C; λ max. KBr. 3.09, 5.67, 5.77 μ; λ max. EtOH 236 mμ (ε19,300).

Provenance & Evidence