Toluene → 8-[2-Fluoro-4-(4'-pentyl-1,1'-bicyclohexane-4-yl)phenyl]-1,4-dioxaspiro[4,5]decan-7-ene

HRID 552030노트

반응식

HRID 552030 반응식
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:25]1(O)[CH2:34][CH2:33][C:28]2([O:32][CH2:31][CH2:30][O:29]2)[CH2:27][CH2:26]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH2:10][CH:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[C:25]1[CH2:34][CH2:33][C:28]2([O:29][CH2:30][CH2:31][O:32]2)[CH2:27][CH:26]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 579964418-[2-Fluoro-4-(4'-pentyl-1,1'-bicyclohexane-4-yl)phenyl]-1,4-dioxaspiro[4,5]decane-8-ol

생성물 1

HCID 579963308-[2-Fluoro-4-(4'-pentyl-1,1'-bicyclohexane-4-yl)phenyl]-1,4-dioxaspiro[4,5]decan-7-ene수율 72.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

The compound (T-5) (29.4g), p-toluenesulfonic acid monohydrate (1.47 g) and toluene (800 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 120 minutes while water being distilled was removed. After cooling to room temperature, the reaction mixture was washed sequentially with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure and the residue was purified by means of column chromatography (silica gel; toluene), giving 8-[2-fluoro-4-(4′-pentyl-1,1′-bicyclohexane-4-yl)phenyl]-1,4-dioxaspiro[4,5]decan-7-ene (T-6) (20.5 g). The yield based on the compound (T-4) was 72%.

후처리

  1. temperatureheated
  2. distillationdistilled
  3. customwas removed
  4. washthe reaction mixture was washed sequentially with water
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
  6. customThe solution obtained
  7. concentrationwas concentrated under reduced pressure
  8. customthe residue was purified by means of column chromatography (silica gel; toluene)

출처 및 근거

ORD 기록
ord-b5122d40dab24543bee057cee0ded400
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951432B2

반응 노트

불러오는 중…