Cyanomethylenetributylphosphorane → HCID 9929326, compound

HRID 748688Notes

Reaction equation

HRID 748688 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]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:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 59750822HCID 59750822, compound

Product 1

HCID 9929326HCID 9929326, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene (20 ml) was dissolved 6-[(4-chlorophenyl)sulfonyl]-6-(2,5-difluorophenyl)-1-hexanol (200 mg, 0.514 mmol). After addition of cyanomethylenetri-n-butylphosphorane (500 mg, 2.07 mmol), the resulting mixture was heated under reflux for 4 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=20:1) to yield a white solid. The resulting solid was washed with hexane/methylene chloride, whereby the title compound (97 mg, 51%) was obtained as a white powder.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 days under an argon atmosphere
  3. temperatureto cool down
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=20:1)
  7. customto yield a white solid
  8. washThe resulting solid was washed with hexane/methylene chloride, whereby the title compound (97 mg, 51%)
  9. customwas obtained as a white powder

Sources & evidence

ORD record
ord-2e6ad2d6eaf94aaabe99f69d0ce66e6b
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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