Tetrahydrofuran → 4-(4-Methylenecyclohexyl)-1,3-benzenediol

반응식

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C[Si]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32](O[Si](C(C)(C)C)(C)C)[C:31]=1[CH:44]1[CH2:49][CH2:48][C:47](=[CH2:50])[CH2:46][CH2:45]1)(C(C)C)C)(C)(C)C.[O:51]1CCCC1>>[CH2:50]=[C:47]1[CH2:48][CH2:49][CH:44]([C:31]2[CH:32]=[CH:33][C:34]([OH:51])=[CH:35][C:30]=2[OH:29])[CH2:45][CH2:46]1

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride2회

HCID 69780056Tert-butyl-[3-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy](isopropyl)dimethylsilane

생성물 1

HCID 98991634-(4-Methylenecyclohexyl)-1,3-benzenediol수율 90%

실험 절차

Tetrabutylammonium fluoride (230 μl) was added to a stirred solution of tert-butyl-[3-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy](isopropyl)dimethylsilane (40 mg) in tetrahydrofuran (2 ml) at room temperature. After 24 hr, further tetrabutylammonium fluoride (50 μl) was added, and after 2 hr the solvent was removed under reduced pressure. The residue was partitioned between water (20 ml) and ethyl acetate (20 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 2:3 v/v) to give the title compound as a white solid (17 mg, 90%). δH(CD3OD) 1.25-1.40 (2H, m), 1.75-1.82 (2H, m), 2.04-2.15 (2H, m), 2.22-2.30 (2H, m), 2.86 (1H, tt), 3.20 (1H, m), 4.50 (2H, s), 6.10-6.16 (2H, m), 6.72 (1H, d); m/z (ES+) 205 (M+H)+.