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

HRID 552030ノート

反応式

HRID 552030 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-b5122d40dab24543bee057cee0ded400
出典データセット
uspto-grants-2011_05
特許番号
US07951432B2

反応ノート

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