Veratroyl chloride → HCID 21182672, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-dimethoxybenzoyl chloride (1.250 g, 6.231 mmol) in 18 miL of chlorobenzene was added 6-benzyloxy-2-(dimethylamino)benzo[b]thiophene (Part B) (1.059 g, 3.738 mmol). The dark blue reaction mixture was then heated to 110° C. and stirred for 17 h by which time the solution turned to brown. The brown solution was then quenched at 0° C. with 30 mL of saturated aqueous NaHCO3 solution and extracted with EtOAc (2×200 mL). The combined organic layers were washed with 200 mL with brine, dried over MgSO4, concentrated under reduced pressure, and purified by flash chromatography (silica gel, 50:50 EtOAc-hexanes) to afford 1.265 g (2.826 mmol, 76%) of a yellow foam.

Provenance & Evidence