Trifluoroacetic acid → HCID 69992966, compound

Participants

Reaction Conditions

Reaction Steps

To 1-(3-methoxy-4-hydroxyethoxy-5-iodophenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol (11.8 g, 21.5 mmol) in chloroform (100 mL) at 0° C. was added dropwise trifluoroacetic acid (9.82 g, 86.1 mmol) in chloroform (100 mL) over 30 minutes. The solution was stirred at 0° C. for 2 hours and then at room temperature for 1 hour. The reaction mixture was quenched with 1N NaOH and chloroform (100 mL) was added. The organic layer was washed with 1N NaOH solution, water and saturated NaCl solution, and then dried over MgSO4, filtered and evaporated in vacuo to an oil which was a cis and trans mixture. The trans isomer was isolated by column chromatography (silica, 1:1 hexane/ethyl acetate) (4.7 g, 41.4%) as the faster eluting isomer. 1H NMR (CDCl3) δ1.99 (m, 2 H); 2.47 (m, 2 H); 3.83 (t, 2 H); 3.84 (s, 3 H); 3.87 (s, 3 H); 3.89 (s, 6 H); 4.16 (t, 2 H); 5.18 (m, 2 H); 6.62 (s, 2 H); 6.96 (d, 1 H); 7.39 (d, 1 H).

Provenance & Evidence