Potassium Phosphate, Dibasic → Ethyl 7,11-dimethyl-3-oxododeca-6,10-dienoate

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Reaction Steps

The sodium salt of ethyl acetoacetate (Compound 11; 20.0 mmol, 3.04 g) was dissolved in 40 ml of tetra hydrofuran (THF) (distilled from sodium/benzophenone ketyl) and cooled to 0° C. n-Butyllithium (2.0 M in cyclohexane, 21.0 mmol, 10.6 ml) was added dropwise to the cooled solution to form a solution of the dianion Compound 12. After 20 minutes, geranyl bromide (Compound 13; 10.0 mmol, 1.98 ml, 2.16 g) was added to the solution of dianion and stirring was continued for an additional 30 minutes at 0° C. The reaction mixture was poured into a cold saturated solution of potassium hydrogen phosphate and extracted with ether (3×20 ml). The combined organic layers were washed with water (20 ml), dried over MgSO4, filtered, and concentrated. Flash chromatography (9:1 hexane/ethyl acetate) afforded 2.05 g (77% yield) of Compound 14 as an oil.

Provenance & Evidence