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Following the procedure of Weiler, J. Am. Chem. Soc. 1974, 96, 1082, benzyl acetoacetate, 7.68 g (40 mmol) was added dropwise to a 0° C. suspension of sodium hydride (2.1 g of 50% dispersion, 42 mmol) in THF (100 mL). After stirring for 10 minutes n-butyl lithium (16 mL of 2.5 M in hexane) was added and the mixture was aged for an additional 10 minutes. At this time iodomethane (2.74 mL, 44 mmol) in THF (4 mL) was added dropwise and the mixture aged 1 hour while slowly warming to room temperature. Work-up was achieved by quenching at 0° C. with 1N HCl, extracting with ether, washing the ether with aqueous NaHCO3, brine, and drying with MgSO4. Removal of the solvent yielded benzyl 3-oxopentanoate.

1. additionwas added
2. waitthe mixture aged 1 hour
3. customby quenching at 0° C. with 1N HCl
4. extractionextracting with ether
5. washwashing the ether with aqueous NaHCO3, brine
6. dry with materialdrying with MgSO4
7. customRemoval of the solvent