Sodium hydride → Z-2-Acetoxy-2-acetyl-5,9-dimethyl-deca-4,8-dienoic acid, tert-butyl ester

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Reaction Steps

tert-butyl 2-acetoxyacetoacetate (B1) (19.5 g, 90 mmol) was added dropwise to a stirred suspension of NaH (2.59 g, 108 mmol) in THF (180 mL) at 0° C. After the liberation of hydrogen gas stopped, nerylbromide (19.6 g, 90 mmol) was added dropwise at 0° C. Afterwards the ice bath was removed and the mixture stirred at room temperature for 16 hours. The resulting mixture was diluted with ether (750 mL), washed with water (3 200 mL) and brine (1 200 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used without further purification.

Provenance & Evidence