Trifluoroacetic acid → HCID 15078315, compound

Participants

Reaction Steps

A solution of 1-[3-(2-hydroxyethylsulfonyl)-4-propoxy-5-benzyloxyphenyl]-4-(3,4,5-trimethoxyphenyl)butan-1,4-diol (from previous experiment) in chloroform (20 mL) was treated with 10% trifluroacetic acid (20 mL). The reaction was monitored by TLC. After 1 h, anhydrous sodium carbonate was added, and the solid was filtered off and washed with chloroform. The solvent was evaporated and the residue was passed through a flash column of silica gel (hexane-ethyl acetate; 2:1, v/v). The cis- and trans-isomers were then separated by HPLC (hexane-ethyl acetate; 1:1, v/v): mp 112°-113° C.; Rf 0.33 (hexane-ethyl acetate; 1:1, v/v); NMR (CDCl3) δ 0.98 (t, J=7.5 Hz, CH2CH2CH3), 1.83 (m, CH2CH2CH3), 2.85 (t, J=6.5 Hz, OH), 3.67 (q, SO2CH2), 3.98 (q, SO2CH2CH2), 4.17 (t, CH2CH2CH3), 5.18 (s, CH2C6H5), 6.63 (s, 2 H, C5ArH).

Provenance & Evidence