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

HRID 748814Notes

Reaction equation

HRID 748814 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])[CH:12]([CH3:17])[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.CCCCCC>[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])[CH2:15][CH2:14][CH2:13][CH:12]2[CH3:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 597508955-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol

Product 1

HCID 597507532-[1-[(4-Chlorophenyl)sulfonyl]-2-methylcyclopentyl]-1,4-difluorobenzeneYield 51%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

The resulting 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol (isomer mixture) was dissolved in toluene (10 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (1.00 g, 4.14 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=20:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with hexane, whereby the title compound (423 mg, 1.14 mmol, 51%) 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=20:1 eluate was concentrated under reduced pressure
  8. customto give a white solid

Sources & evidence

ORD record
ord-3c7733dae09c46d281552842ed396cb9
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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