Potassium Carbonate → Ethyl 4-[4-(ethylmethanesulfonylamino)-2,2-dimethylchroman-6-yloxy]valerate

Participants

Reaction Conditions

Reaction Steps

1.5 g (5 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethylmethane-sulfonamide (Example 1g) were stirred at 80° C. for 30 min with 0.7 g of powdered potassium carbonate in 75 ml of DMA. 0.8 ml (5 mmol) of ethyl 5-bromovalerate was then added and the mixture was stirred at 120° C. for 120 min. After reaction was complete (TLC), the mixture was concentrated in vac., treated with ice water and aqueous hydrochloric acid and a crystalline crude product was obtained, which was chromatographed on silica gel using n-heptane/EA (2:1). Appropriate fractions were crystallized using petroleum ether, 1.5 g, m.p. 65-67° C.

Provenance & Evidence