Methyl acetoacetate → HCID 2727782, compound

Participants

Reaction Steps

4-Fluorobenzaldehyde (0.997 mL, 9.30 mmol, 1.00 equiv), 2,2-dimethyl-1,3-dioxane-4,6-dione (1.34 g, 9.30 mmol, 1.00 equiv), methyl acetoacetate (1.00 mL, 9.30 mmol, 1.00 equiv), and ammonium acetate (0.752 g, 9.77 mmol, 1.05 equiv) were dissolved in acetic acid (10 mL) and heated to reflux for 3.5 hours. The reaction mixture was diluted with EtOAc and water, and neutralized with 2N NaOH. The phases were separated, and the organic phase was washed with satd. NaHCO3, then NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to a yellow residue. Recrystallization (CH2Cl2/hexanes) provided 480 mg (20%) of the product as a pale yellow solid. MS (ES+) m/e 264 [M+H]+.

Provenance & Evidence