Diethylene glycol vinyl ether → 2-[1-[(4-Chlorophenyl)sulfonyl]-3-(2-vinyloxyethoxy)propyl]-1,4-difluorobenzene

HRID 748689Notes

Reaction equation

HRID 748689 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(C=P(CCCC)(CCCC)CCCC)#N.[CH:36]([O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43]O)=[CH2:37]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH2:43][CH2:42][O:41][CH2:40][CH2:39][O:38][CH:36]=[CH2:37])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13581Diethylene glycol vinyl etherHCID 4622928Cyanomethylenetributylphosphorane2×HCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 597507682-[1-[(4-Chlorophenyl)sulfonyl]-3-(2-vinyloxyethoxy)propyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene (30 ml) was dissolved the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (520 mg, 1.72 mmol) obtained in Example 5. After addition of 2,2-(2-vinyloxyethoxy)ethanol (0.270 ml, 2.10 mmol) and cyanomethylenetri-n-butylphosphorane (500 mg, 2.07 mmol), the mixture was heated under reflux for 24 hours under an argon atmosphere. The reaction mixture was then allowed to cool down. After addition of 2-(2-vinyloxyethoxy)-ethanol (0.170 ml, 1.25 mmol) and cyanomethylenetri-n-butylphosphorane (300 mg, 1.24 mmol), the mixture was heated under reflux for 12 hours under an argon atmosphere. The reaction mixture was allowed to cool down and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=7:1) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (140 mg, 20%) was obtained as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours under an argon atmosphere
  3. temperatureto cool down
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 12 hours under an argon atmosphere
  6. temperatureto cool down
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel chromatography (hexane:ethyl acetate=7:1)
  10. customto yield a white solid
  11. washThe resulting white solid was washed with hexane, whereby the title compound (140 mg, 20%)
  12. customwas obtained as a white powder

Sources & evidence

ORD record
ord-a9ebf1a3b67445a0ace7f5f4238e70b6
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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