Hydrochloric Acid → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(3-carbomethoxyphenylethynyl)cyclohexan-1-one

Participants

Reaction Steps

A solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(3-carbomethoxyphenylethynyl)cyclohexane (0.060 g, 0.12 mmol) in tetrahydrofuran (5 mL) containing 3N hydrochloric acid (0.60 mL) under an argon atmosphere was heated at 55°-60° C. for 2 h. The cooled reaction mixture was partitioned between ice cold dilute aqueous sodium carbonate solution and ethyl acetate. The organic phase was washed with water, saturated brine, was dried over sodium sulfate, and was concentrated in vacuo. The residue was chromatographed (silica gel), eluting with 15% ethyl acetate/hexanes, to afford a resin. Anal. (C28H30O5.1/4 H2O) calcd: C 74.56, H 6.82, found: C 74.43, H 6.80. 1H-NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 8.00 (d-d, J=1.5 Hz;J=6.6 Hz, 1H), 7.65 (d-d, J=1.3 Hz, J=7.7 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.21 (d, J=2.1, 1H), 7.12 (d-d, J=2.0 Hz, J=8.5 Hz, 1H), 6.87 (d, J=8.5 Hz,1H), 4.81 (m, 1H), 3.94 (s, 3H), 3.86 (s, 3H), 3.04 (d-t, J=6.0 Hz, J=14.2, 2H), 2.50 (d,br, J=14.8, 2H), 2.4-2.2 (m, 4H), 2.0-1.5 (m).

Provenance & Evidence