Hydrochloric Acid → HCID 15392033, compound

Participants

Reaction Steps

A solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(3-carboxyphenylethynyl)cyclohexane (0.11 g, 0.23 mmol) in tetrahydrofuran (6 mL) containing 3N hydrochloric acid (0.7 mL) was heated under an argon atmosphere at 55°-70° C. for 2 h. The cooled reaction mixture was concentrated in vacuo and the residue was partitioned between cold water and methylene chloride. The organic phase was washed with saturated brine solution, was dried over magnesium sulfate and was evaporated. The residue was chromatographed (silica), eluting with methylene chloride/methanol/water (90/5/0.25 to 90/10/0.5) and was concentrated in vacuo. The residue was dissolved in methanol and was foamed in vacua to afford a white fractured glass. Anal. (C27H28O5.1/4 H2O.1/4 CH3OH) calcd: C 73.55, H 6.68, found: C 73.51, H 6.66. 1H-NMR (400 MHz, CDCl3) δ 8.22 (t, J=1.5 Hz, 1H), 8.09 (d-d, J=1.3 Hz;J=7.9 Hz, 1H), 7.72 (d-d, J=1.3 Hz, J=7.8 Hz, 1H), 7.47 (t, J=7.8 Hz, 1H), 7.22 (d, J=2.2, 1H), 7.13 (d-d, J=2.3 Hz, J=8.4 Hz, 1H), 6.88 (d, J=8.5 Hz,1H), 4.82 (p, 1H), 3.86 (s, 3H), 3.25 (d, J=20 Hz, CH3OH, 0.55H), 3.04 (d-t, J=5.8 Hz, J=14.5, 1.7H), 2.50 (d,br, J=14.8, 1.8H), 2.4-2.2 (m, 4H), 2.0-1.5 (m).

Provenance & Evidence