Water → HCID 178455766, compound

HRID 2241797Notes

Reaction equation

HRID 2241797 reaction equation
CS([O:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH:19]=[CH2:20])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1)(=O)=O.[F:21][C:22]1[C:27]([F:28])=[C:26]([O:29][CH2:30][CH3:31])[CH:25]=[CH:24][C:23]=1O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C>[CH2:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([O:5][CH2:6][C@H:7]2[CH2:12][CH2:11][C@H:10]([C@H:13]3[CH2:18][CH2:17][C@H:16]([CH:19]=[CH2:20])[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)=[C:22]([F:21])[C:27]=1[F:28])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 144957634-Ethoxy-2,3-difluorophenolHCID 178455773HCID 178455773, compound

Product 1

HCID 178455766HCID 178455766, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

9.8 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethyl methanesulfonate and 5.96 g of 2,3-difluoro-4-ethoxyphenol were dissolved in 90 mL of DMF. 10.4 g of tripotassium phosphate was added, followed by stirring at 90 to 100° C. for 3 hours. The reaction mixture was poured into water, extracted with toluene, washed in turn with water, 10% hydrochloric acid, water, and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified in turn by subjecting to column chromatography (silica gel/toluene), recrystallization (methanol/acetone), column chromatography (alumina/acetone), washing with ion-exchange water, silica treatment, and recrystallization (methanol/acetone) to obtain 8.5 g of 4-ethoxy-2,3-difluoro-1-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxybenzene (IIIa) as a colorless crystal.

Workup

  1. extractionextracted with toluene
  2. washwashed in turn with water, 10% hydrochloric acid, water, and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified in turn
  6. customby subjecting to column chromatography (silica gel/toluene), recrystallization (methanol/acetone), column chromatography (alumina/acetone)
  7. washwashing with ion-exchange water, silica treatment, and recrystallization (methanol/acetone)

Sources & evidence

ORD record
ord-29d12be847a341e990b33ff76fa13b8a
Source dataset
uspto-grants-2010_03
Patent number
US07670504B2

Reaction notes

Loading…