Dimethylformamide → HCID 9930603, compound

Participants

Reaction Steps

To an ice-cooled stirred solution of the product from Example 52 step a (725 mg, 3.00 mmol) in DMF (9 ml) was added, in a single portion, sodium hydride (60% dispersion in mineral oil, 144 mg, 3.60 mmol). The coolant was removed and the suspension was stirred at ambient temperature for 30 minutes. The suspension was cooled in ice and 1,5-dibromopentane (1.23 ml, 9.03 mmol) was added in three portions. The coolant was removed and the reaction mixture was stirred at ambient temperature for 18 h. The reaction was quenched with water (40 ml) and then extracted with ethyl acetate (40 ml). The aqueous phase was discarded and the organic phase washed twice with brine (40 ml). The organic phase was dried over anhydrous magnesium sulfate and the filtrate evaporated at reduced pressure. The residue was purified by flash column chromatography (5:1 hexane:ethyl acetate) to afford the title product.

Provenance & Evidence