Tetrahydro-4H-pyran-4-ol → 4-[(4-Chlorobenzene-1-sulfonyl)(oxan-4-yl)methyl]pyridine

HRID 748731Notes

Reaction equation

HRID 748731 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.[O:18]1[CH2:23][CH2:22][CH:21](O)[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:21]2[CH2:22][CH2:23][O:18][CH2:19][CH2:20]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 74956Tetrahydro-4H-pyran-4-ol2×HCID 4622928Cyanomethylenetributylphosphorane2×HCID 230286434-(4-Chlorophenylsulfonylmethyl)pyridine

Product 1

HCID 231147154-[(4-Chlorobenzene-1-sulfonyl)(oxan-4-yl)methyl]pyridineYield 71%

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, tetrahydropyran-4-ol (51 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 tetrahydropyran-4-ol (51 μl, 0.538 mmol) and cyanomethylenetri-n-butylphosphorane (129 mg, 0.538 mol), followed by heating 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 (=1:2) eluate was concentrated under reduced pressure to give the title compound (65 mg, 71%) 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. temperatureby heating
  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 (=1:2) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ad47b2c18124721a7c1e0e939e5f419
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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