Cyanomethylenetributylphosphorane → HCID 59750738, compound

HRID 748794Notes

Reaction equation

HRID 748794 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][S: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.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])[CH2:16][CH2:15][S:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 59750752HCID 59750752, compound

Product 1

HCID 59750738HCID 59750738, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

In toluene (50 ml) was dissolved 2-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propylthio]ethanol (800 mg, 2.00 mmol), followed by the addition of cyanomethylenetri-n-butylphosphorane (1.50 g, 6.22 mmol). Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. After the reaction mixture was allowed to cool down, it was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=15:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with hexane, whereby the title compound (504 mg, 1.28 mmol, 64%) 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. concentrationit was concentrated under reduced pressure
  5. customthe fraction obtained from the hexane
  6. concentrationethyl acetate=15:1 eluate was concentrated under reduced pressure
  7. customto give a white solid

Sources & evidence

ORD record
ord-87619fec0ec3486eaab777853e9737a4
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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