1-Bromopentane → 2-Acetoxy-2-acetyl-heptanoic-acid-tert-butylester

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Reaction Steps

According to the general alkylation method, tert-butyl-2-acetoxy-aceto-acetate (219a) (7.12 g, 32.9 mmol), NaH (900 mg, 37.5 mmol) and pentylbromide (4.97 g, 32.9 mmol) were reacted in DMF (64 mL) to give 2-acetoxy-2-acetyl-heptanoic-acid-tert-butylester (250j) (6.40 g, 22.3 mmol, 68%) as a slightly yellow oil after Kugelrohr distillation at 185° C. and 1.0 mbar. Then, 250j (6.40 g, 22.3 mmol) and 402 mg (2.11 mmol) p-TsOH.H2O were stirred in 65 mL benzene according to decarboxylation method A. Kugelrohr distillation at 1.0 mbar and 125° C., followed by column chromatography (ethyl acetate:petroleum ether=1:4) gave 251j (1.6 g, 8.59 mmol, 39%) as a colorless oil.

Provenance & Evidence