反应详情

To an ice-water cooled mixture of 1,1-dimethylethyl(2E)-3-{4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoate (10) (4.42 g, 10.9 mmol) and CH2Cl2 (20 mL) was slowly added trifluoroacetic acid (10 mL) with stirring under a nitrogen atmosphere. After 3 h, the reaction mixture was filtered. The filtered solid was washed with CH2Cl2 and dried to give 2.2 g of compound 11 as a white solid. The filtrate was concentrated and the impure product was partially purified by flash chromatography on silica gel with CH2Cl2:MeOH (100:0 to 9:1) to give a yellow solid. The solid was triturated with Et2O and the suspension was filtered. The filtered solid was dried to give a second crop of compound 11 (354 mg) as a pale tan solid. The Et2O filtrate noted above was concentrated in vacuo and the impure product was crystallized from hexanes and EtOAc. The solid was dried to give a third crop of compound 11 (185 mg) as a pale tan solid. The total yield of 11 was 2.74 g (72%). Analytical data for all three batches were comparable. The analytical data is herein presented for the first batch. 1H NMR (400 MHz, DMSO-d6): δ 1.50 (m, 8 H), 2.21 (m, 4 H), 6.43 (d, J=15.9 Hz, 1 H), 6.65 (d, J=8.4 Hz, 2 H), 6.90 (d, J=8.5 Hz, 2 H), 7.11 (d, J=8.0 Hz, 2 H), 7.52 (d, J=16.1 Hz, 1 H), 7.57 (d, J=8.0 Hz, 2 H), 9.28 (s, 1 H), 12.21 (br s, 1 H). LRMS (ESI): m/z 347 (M−H)−. Anal. Calcd for C23H24O3: C, 79.28; H, 6.94. Found: C, 79.16; H, 6.97.

1. filtrationthe reaction mixture was filtered
2. washThe filtered solid was washed with CH2Cl2
3. customdried