Lithium diisopropylamide → 2-Ethoxy4-methyl-4-phenylhex-2-enoic acid ethyl ester

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Reaction Steps

To a chilled (0° C.) solution of 7.4 g of (diethoxyphosphoryl)ethoxy acetic acid ethyl ester in 30 mL of THF was added 16 mL of a 1.8M solution of LDA. After 30 minutes, 4.2 g of 2-methyl-2-phenylbutyraldehyde in 30 mL of THF was added dropwise by syringe. The mixture was warmed to room temperature, quenched with saturated aqueous ammonium chloride, and extracted with diethyl ether. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to afford 8.3 g of 2-ethoxy4-methyl-4-phenylhex-2-enoic acid ethyl ester as an orange oil and a mixture of geometric isomers (2:1).

Provenance & Evidence