Diethyl Oxalate → Ethyl 4-(adamantan-1-yl)-2,4-dioxobutanoate

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Reaction Steps

Preparation C13, Step 1: Diethyl oxalate (3.81 mL, 28 mmol, 1 eq.) was dissolved in THF (25 mL) at RT under nitrogen then taken to near-reflux. Sodium hydride (1.18 g, 29 mmol, 1.05 eq.) was added in 5 portions carefully. A solution of 1-adamantyl methyl ketone (5.00 g, 28 mmol, 1 eq.), in THF (10 mL) was added dropwise via an addition funnel. After the addition was complete, the mixture was refluxed for 1 hour. Cooled to RT and very carefully quenched with saturated NH4Cl (50 mL) then extracted 3 times with methylene chloride. The organic layers were combined, dried and stripped in vacuo to give 7.80 g of 4-adamantan-1-yl-2,4-dioxo-butyric acid ethyl ester as an amber oil. MS found: (M+H)+=279.

Provenance & Evidence