Water → HCID 74018133, compound

HRID 2260914Notes

Reaction equation

HRID 2260914 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]1[C:19]([F:20])=[C:18]([O:21][CH2:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:15]=1[CH:25](O)[CH2:26][CH:27]1[CH2:32][CH2:31][CH:30]([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:35][CH2:34]2)[CH2:29][CH2:28]1.O>C1(C)C=CC=CC=1>[F:13][C:14]1[C:19]([F:20])=[C:18]([O:21][CH2:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:15]=1[CH:25]=[CH:26][CH:27]1[CH2:32][CH2:31][CH:30]([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:35][CH2:34]2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 962Water2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 23118844HCID 23118844, compound

Product 1

HCID 74018133HCID 74018133, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.16 g of p-toluenesulfonic acid monohydrate was added to the compound (9) having been dissolved in 60 mL of toluene, and the mixture was heated under stirring by using a Dean-Stork trap until completion of azeotrope of water. After terminating the reaction by adding water, the aqueous layer was extracted with toluene, washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography and then subjected to recrystallization to obtain 11.2 g of 1-(2,3-difluoro-4-ethoxy-6-methylphenyl)-2-(4-(4-pentylcyclohexyl)cyclohexyl)ethene (Compound 1-3-3-10) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. customAfter terminating
  3. customthe reaction
  4. extractionthe aqueous layer was extracted with toluene
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography
  9. customsubjected to recrystallization

Sources & evidence

ORD record
ord-05e57ea1487042bdaa976de0389fb4e2
Source dataset
uspto-grants-2010_12
Patent number
US07846513B2

Reaction notes

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