Water → HCID 178455767, compound

HRID 1674435Notes

Reaction equation

HRID 1674435 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C@H:17]3[CH2:22][CH2:21][C@H:20]([CH:23]=[CH2:24])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH:5]=[CH:4][C:3]=1[OH:25].[CH2:26]([C@H:28]1[CH2:33][CH2:32][C@H:31]([CH2:34]Br)[CH2:30][CH2:29]1)[CH3:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([C@H:17]3[CH2:22][CH2:21][C@H:20]([CH:23]=[CH2:24])[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)[CH:5]=[CH:4][C:3]=1[O:25][CH2:34][C@H:31]1[CH2:32][CH2:33][C@H:28]([CH2:26][CH3:27])[CH2:29][CH2:30]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 178455729HCID 178455729, compoundHCID 178455768HCID 178455768, compound

Product 1

HCID 178455767HCID 178455767, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

6.5 g of 2,3-difluoro-4-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxyphenol was dissolved in 35 mL of DME, and 4.9 g of (trans-4-ethylcyclohexyl)methyl bromide and 6.4 g of tripotassium phosphate were added thereto, and then stirred for 2 hours at 80 to 100° C. Water and toluene were added thereto, and the organic layer was fractioned. The resultant product was washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by recrystallization and column chromatography, to thereby obtain 3.8 g of 2,3-difluoro-1-(trans-4-ethylcyclohexyl)methoxy-4-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxybenzene (1a) in the form of colorless crystals.

Workup

  1. washThe resultant product was washed with saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by recrystallization and column chromatography

Sources & evidence

ORD record
ord-e0606c40310444a0acc7b7d8fe5eb752
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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