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

HRID 552030Notes

Reaction equation

HRID 552030 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%.

Workup

  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)

Sources & evidence

ORD record
ord-b5122d40dab24543bee057cee0ded400
Source dataset
uspto-grants-2011_05
Patent number
US07951432B2

Reaction notes

Loading…