Cyclohexylisopropylamine → Lithium cyclohexylisopropylamide

Participants

Reaction Steps

Lithium N-isopropyl-N-cyclohexylamide was prepared at -78° in anydrous THF from n-butyl lithium (6.1 mmol) and N-isopropyl-N-cyclohexylamine (1.00 ml). Ethyl trimethylsilylacetate (1.1 ml) was added, followed after 10 minutes by addition of the above ketone in THF. The reaction mixture was left at room temperature for 16 hours and worked-up in the usual manner. Excess ethyl trimethylsilylacetate was removed in vacuo and purification by column chromatography on silica (9:1, hexane: ether) gave (2E/Z)ethyl 3-methyl-12-(2-quinolinyloxy)dodec-2-enoate (0.33 g). This was converted to the title compound by analogy with Stages c and d of EXAMPLE I.

Provenance & Evidence