Diisopropylamine → Ethyl 2-benzylideneamino-2-ethylhexanoate

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Reaction Steps

A 1.6M solution of n-butyl lithium in hexane (33 mmoles, Aldrich) was added to a solution of diisopropylamine (40 mmoles) in THF (21 ml) at a temperature of 5°-10° C. When addition was complete, the mixture was added to a solution of the product from step (b) (30 mmoles) in THF (20 ml) at a temperature of 5°-10° C. When addition was complete, n-butyl iodide (40 mmoles) was added and the mixture allowed to warm to room temperature. After 20 hours, the mixture was poured into water/diethyl ether (1.1 L/0.5 L) and the organic layer separated, washed with brine (1.1 L), dried and evaporated in vacuo to give the desired product as an amber liquid (100% yield).

Provenance & Evidence