Pentane → HCID 18931279, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-1-iodobutane (30 g, 137.6 mmol), ether (300 mL) and pentane (500 mL) was cooled to approximately -65° C. and then tert-butyllithium (1.7M, 160 mL, 0.27 moles) was added over 30 minutes such that the reaction mixture remained below approximately -55° C. The mixture was cooled 1 hour with stirring at -65° C. to -60° C. and then N-methoxy-N-methyl-5-chloro-2-methoxybenzamide (25 g, 0.11 mol), prepared as in Example 4, in THF (approximately 80 mL) was added. The mixture was diluted with additional ether (300 mL), allowed to warm to 10° C. and then combined with saturated ammonium chloride. The organic layer was separated, dried (K2CO3), filtered and concentrated. The residue was purified by column chromatography eluding with hexane/ethyl acetate (9:1 to 85:15) to give 5-chloro-1-(5-chloro-2-methoxy-phenyl)-1-pentanone, m.p. 52°-54° C.

Provenance & Evidence