2-Pentanol → HCID 59750756, compound

HRID 748826Notes

Reaction equation

HRID 748826 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:20][CH:21](O)[CH2:22][CH2:23][CH3:24].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]([CH:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH:21]([CH3:20])[CH2:22][CH2:23][CH3:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 223862-PentanolHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 59750756HCID 59750756, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (200 mg, 0.661 mmol) obtained in Example 5 and 2-pentanol (0.144 ml, 1.33 mmol) were dissolved in toluene (3 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (0.320 ml). Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. The reaction mixture was then allowed to cool down. The residue obtained by concentrating the reaction mixture under reduced pressure was separated and purified by flash silica gel chromatography (hexane:ethyl acetate=50:1), whereby obtained were the title Isomer 292-A (low polarity) (67 mg, 0.18 mmol, 27%) as a white powder and the title Isomer 292-B (high polarity) (45 mg, 0.12 mmol, 19%) as a white solid.

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. customwas separated
  7. custompurified by flash silica gel chromatography (hexane:ethyl acetate=50:1), whereby
  8. customobtained

Sources & evidence

ORD record
ord-9ac101cc943b45f3ba5ed58743920e97
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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