Butyl bromide → 2-Acetoxy-2-acetyl-hexanoic-acid-tert-butylester

Participants

Reaction Steps

According to the general alkylation method, tert-butyl-2-acetoxy-aceto-acetate (219a) (1.08 g, 5.00 mmol), NaH (156 mg, 6.5 mmol) and butylbromide (538 μL, 685 mg, 5.00 mmol) were reacted in DMF (10 mL) to give 2-acetoxy-2-acetyl-hexanoic-acid-tert-butylester (250i) (1026 mg, 3.77 mmol, 75%) as a slightly yellow oil. Then, 250i (731 mg, 2.68 mmol) and 51 mg (0.27 mmol) p-TsOH.H2O were stirred in 9.0 mL benzene according to decarboxylation method A. Kugelrohr distillation at 1.0 mbar and 60° C. gave 251i (415 mg, 2.41 mmol, 90%) as a colorless oil.

Provenance & Evidence