Hexamethylphosphoramide → HCID 272210, compound

Participants

Reaction Steps

A solution of 10.00 g (45 mmol, Aldrich) of 6-bromo-2-naphthol and 2.16 g (49.0 mmol, 1.1 eq. 60% in oil, Aldrich) of NaH dispersion in 100 ml of dry THF was stirred at 0° C., until gas evolution ceased. A solution of 4.60 ml (45.0 mmol, Aldrich) of 4-bromo-1-butene in 25 ml of DMF was added dropwise and the solution was warmed to room temperature, then stirred at 70° C. overnight. To this solution was added 2.28 ml (22.5 mmol, 0.5 eq., Aldrich) of 4-bromo-1-butene and 6 ml of hexamethylphosphoric triamide (HMPA). Then 1.00 g (20.8 mmol, 60% in oil, Aldrich) of NaH dispersion in 10 ml of dry THF was added, stirred at 70° C. for 8 hours and finally heated to 90° C. for 12 hours. The mixture was cooled, water was added, this was extracted with EtOAc, dried (MgSO4) and concentrated in vacuo. Purification was achieved via flash chromatography (silica gel, 1:8 EtOAc/petroleum ether) to yield 4.31 g (35%) of title compound as a bright yellow solid, m.p. 35°-37° C.

Provenance & Evidence