Diethyl Ether → HCID 15078330, compound

Participants

Reaction Steps

A mixture of trans-2-[3-(2-hydroxyethylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (183 mg, 0.37 mmol), chloroacetone (0.033 mL, 0.41 mmol) and potassium carbonate (162 mg, 1.17 mmol) in DMF (3 mL) was stirred at room temperature overnight. Ethyl ether and water were added and the aqueous layer was re-extracted with ether (2 x). The organic extracts were combined, dried, and evaporated to a syrup, which was purified by preparative TLC (hexane-ethyl acetate; 1:2, v/v) to give the title compound Rf 0.33; NMR (CDCl3) δ 1.06 (t, CH2CH2CH3), 2.33 (s, CH2COCH3), 3.66 (q, SO2CH2CH2), 3.97 (b, SO2CH2CH2) 4.20 (t, CH2CH2CH3), 4.68 (s, CH2COCH3), 5.12-5.28 (m, H-2 & H-5), 6.62 (s, 2 H, C5ArH), 7.17 & 7.56 (2 d, 2 H, C2ArH).

Provenance & Evidence