Cyanomethylenetributylphosphorane → 2-[1-[(4-Chlorophenyl)sulfonyl]cyclopentyl]-1,4-difluorobenzene

HRID 748685Notes

Reaction equation

HRID 748685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH2:12][CH2:13][CH2:14][CH2:15]O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[F:24])[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4622928Cyanomethylenetributylphosphorane2×HCID 597508325-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-1-pentanol

Product 1

HCID 597509152-[1-[(4-Chlorophenyl)sulfonyl]cyclopentyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene (10 ml) was dissolved 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-1-pentanol (100 mg, 0.267 mmol). After addition of cyanomethylenetri-n-butylphosphorane (130 mg, 0.539 mmol), the mixture was heated under reflux for 2 days under an argon atmosphere. The reaction mixture was allowed to cool down and then, added with cyanomethylenetri-n-butylphosphorane (130 mg, 0.539 mmol). The mixture was heated under reflux for 3 days 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=15:1) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (35 mg, 37%) was obtained as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 days under an argon atmosphere
  3. temperatureto cool down
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 3 days 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=15:1)
  10. customto yield a white solid
  11. washThe resulting white solid was washed with hexane, whereby the title compound (35 mg, 37%)
  12. customwas obtained as a white powder

Sources & evidence

ORD record
ord-0dfd38197a0b415abaf5b239ad4c5ed3
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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