4-Toluenesulfonyl chloride → (4E)-5-(3-Pyridyl)-4-pentene-2-ol p-Toluenesulfonate

HRID 968385Notes

Reaction equation

HRID 968385 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[CH2:9][CH:10]([OH:12])[CH3:11])[CH:2]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:12][CH:10]([CH2:9]/[CH:8]=[CH:7]/[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH3:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12042974(4E)-5-(3-Pyridyl)-4-penten-2-ol

Product 1

HCID 87466987(4E)-5-(3-Pyridyl)-4-pentene-2-ol p-ToluenesulfonateYield 60.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (4E)-5-(3-pyridyl)-4-penten-2-ol (5.00 g, 30.67 mmol) in dry pyridine (30 mL) at 0° C. was added p-toluenesulfonyl chloride (8.77 g, 46.01 mmol). The reaction mixture was stirred for 24 h at ambient temperature. The pyridine was removed by rotary evaporation. Toluene (50 mL) was added to the residue and subsequently removed by rotary evaporation. The crude product was stirred with a saturated solution of sodium bicarbonate (100 mL) and extracted with chloroform (3×100 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography over aluminum oxide, eluting with ethyl acetate-hexane (3:7, v/v). Selected fractions were combined and concentrated by rotary evaporation to give a viscous, brown oil (5.83 g, 60.1%).

Workup

  1. customThe pyridine was removed by rotary evaporation
  2. additionToluene (50 mL) was added to the residue
  3. customsubsequently removed by rotary evaporation
  4. stirringThe crude product was stirred with a saturated solution of sodium bicarbonate (100 mL)
  5. extractionextracted with chloroform (3×100 mL)
  6. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe crude product was purified by column chromatography over aluminum oxide
  10. washeluting with ethyl acetate-hexane (3:7, v/v)
  11. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-52ecf0ceb00041558f01ccb9db67ec30
Source dataset
uspto-grants-2005_10
Patent number
US06958399B2

Reaction notes

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