1-Iodopentane → HCID 14350139, compound

Participants

Reaction Conditions

Reaction Steps

To 2.2 g (63 mmol) of the silylacetylene of Example 2 dissolved in 50 ml of dry THF and cooled to -78° C. under argon was added dropwise 5.6 ml (7.0 mmol) of a 1.25M solution of methyl lithium in diethyl ether. Upon addition, the reaction was warmed to -10° C. and stirred at -10° C. for 30 min. Iodopentane (1.2 ml, 9.0 mmol) was then added followed by 5.0 ml of hexamethylphosphoric triamide (HMPA) whereupon the reaction mixture was warmed to R.T. and stirred overnight. The reaction was quenched with about 5.0 ml of H2O, then poured into hexane and washed 4× with H2O, and 1× with brine. The organic layer was dried (MgSO4) and the solvent removed to yield a dark red oil which was purified by medium pressure liquid chromotography (MPLC) eluting with hexane to yield 2.14 g of the titled product as a pale yellow oil.

Provenance & Evidence