Cyclopentanol → 4-[(4-Chlorobenzene-1-sulfonyl)(cyclopentyl)methyl]pyridine

HRID 748730Notes

Reaction equation

HRID 748730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:18]1(O)[CH2:22][CH2:21][CH2:20][CH2:19]1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7298Cyclopentanol2×HCID 4622928Cyanomethylenetributylphosphorane2×HCID 230286434-(4-Chlorophenylsulfonylmethyl)pyridine

Product 1

HCID 597508864-[(4-Chlorobenzene-1-sulfonyl)(cyclopentyl)methyl]pyridineYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene (5 ml) solution of the 4-(4-chlorophenylsulfonylmethyl)pyridine (70 mg, 0.261 mmol) obtained in Example 119, cyclopentanol (49 μl, 0.538 mmol) and cyanomethylenetri-n-butylphosphorane (129 mg, 0.538 mol) was heated under reflux for 3 days under an argon atmosphere. After cooling to room temperature, the reaction mixture was added with cyclopentanol (49 μl, 0.538 mmol) and cyanomethylenetri-n-butylphosphorane (129 mg, 0.538 mol). The mixture was heated under reflux for 22 hours under an argon atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure to give the title compound (77 mg, 88%) as a white solid. The resulting solid was washed with hexane-ether and collected by filtration, whereby the title compound was obtained as a white powder.

Workup

  1. temperatureunder reflux for 3 days under an argon atmosphere
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 22 hours under an argon atmosphere
  4. temperatureAfter cooling to room temperature
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. customthe fraction obtained from the hexane
  7. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-87310c12ee194aef8ae97cada21f54f3
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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