4-Toluenesulfonyl chloride → HCID 9794668, compound

Participants

Reaction Conditions

Reaction Steps

p-Toluenesulfonyl chloride (1.91 g, 10.0 mmol) was added, in one portion, to a stirred solution of (4E)-5-(4-methyl-3-nitropheny)-4-penten-2-ol (1.70 g, 7.69 mmol) in triethylamine (5 mL) and dichloromethane (10 mL) at 10° C. under nitrogen. The cooling bath was removed, and the mixture was stirred at 25° C. for 16 h. Saturated aqueous NaHCO3 (10 mL) was then added and the biphasic mixture was vigorously stirred for 2 h. The layers were separated and the aqueous layer was extracted once with dichloromethane (10 mL). The combined organic layers were dried (Na2SO4) and evaporated, and the residue was combined with DMF (7 mL) and 40% aqueous methylamine (20 mL). This mixture, also biphasic, was vigorously stirred at 25° C. for 18 h, poured into a mixture of 30% aqueous NaOH (2 mL) and saturated aqueous NaCl (50 mL), and extracted with ether (3×30 mL). The ether extracts were dried (Na2SO4) and evaporated, and the residue was column chromatographed on 100 g of Merck silica gel 60 (70-230 mesh) with 5% (v/v) methanol, 5% triethylamine (v/v) in benzene. This gave 453 mg (25.2% yield) of yellow oil.

Provenance & Evidence