1,2-Dibromoethane → HCID 15078312, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Dibromoethane (1.12 mL, 13 mmol) was added to a solution of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (331 mg, 0.65 mmol) (Example 18) in DMF (5 mL) containing potassium carbonate (550 mg, 3.9 mmol). The reaction mixture was heated with stirring at 70° C. for 7 h and, cooled, and partitioned between ethyl ether and water. The ethereal layer was separated and the aqueous layer was re-extracted twice with ether. The organic extracts were combined, dried, and evaporated to dryness. The product was purified by flash column chromatography on silica gel using hexane-ethyl acetate (2:1, v/v) as the eluant: Rf 0.42 (hexane-ethyl acetate; 1:2, v/v); NMR (CDCl3) δ 1.06 (t, CH2CH2CH3), 1.25 (d, CH2CHOHCH3), 1.90 (m, CH2CH2CH3), 3.74 (t, CH2CH2Br), 3.83 (s, OCH3) 3.88 (s, 2 OCH3), 5.16-5.28 (m, H-2 and H-5), 6.62 (s, 2 H, C5ArH), 7.28 and 7.54 (2 d, 2 H, C2ArH).

Provenance & Evidence