1-Bromopropane → HCID 15078318, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-2-[3-(2-hydroxyethylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (366 mg, 0.74 mmol), n-propyl bromide (0.12 mL, 1.33 mmol) and potassium carbonate (255 mg, 1.85 mmol) in DMF (3 mL) was heated at 75° C. for 1 h. The reaction mixture was cooled and partitioned between ethyl ether and water, and the aqueous layer was re-extracted with ether (2 x). The organic extracts were combined, dried, and evaporated to dryness. The residue was purified by chromatography to give the title compound: Rf 0.43 (hexane-ethyl acetate; 1:2, v/v); NMR (CDCl3) δ 1.05 & 1.09 (2 t, J=7.5 Hz, 2 CH2CH2CH3), 2.85 (t, J=6.5 Hz, OH), 3.65 (m, SO2CH2), 3.95 (m, SO2CH2CH2); 4.03 & 4.15 (2 t. J=6.5 Hz, 2 CH2CH2CH3), 6.63 (s, 2 H, C5ArH), 7.27 & 7.49 (2 d, J=1.5 Hz, C2ArH).

Provenance & Evidence