Cyanomethylenetributylphosphorane → HCID 59750743, compound

HRID 748810Notes

Reaction equation

HRID 748810 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 59750809HCID 59750809, compound

Product 1

HCID 59750743HCID 59750743, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

In toluene (5 ml) was dissolved 7-[(4-chlorophenyl)sulfonyl]-7-(2,5-difluorophenyl)-1-heptanol (200 mg, 0.496 mmol), followed by the addition of cyanomethylenetri-n-butylphosphorane (400 mg, 1.66 mmol). Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. After the reaction mixture was allowed to cool down, the residue obtained by concentrating the reaction mixture under reduced pressure was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=10:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with hexane, whereby the title compound (111 mg, 0.288 mmol, 58%) was obtained as a white powder.

Workup

  1. temperatureUnder an argon atmosphere, the resulting mixture was heated
  2. temperatureunder reflux for 14 hours
  3. temperatureto cool down
  4. customthe residue obtained
  5. concentrationby concentrating the reaction mixture under reduced pressure
  6. customThe fraction obtained from the hexane
  7. concentrationethyl acetate=10:1 eluate was concentrated under reduced pressure
  8. customto give a white solid

Sources & evidence

ORD record
ord-a25ac964db4a46c5b4e7c13d716a9db9
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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