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

HRID 2064286Notes

Reaction equation

HRID 2064286 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[CH2:9][C@H: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][C@@H: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 66745560(2R)-(4E)-5-(3-pyridyl)4-penten-2-ol

Product 1

HCID 87466997(2R)-(4E)-5-(3-Pyridyl)4-penten-2-ol p-Toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of (2R)-(4E)-5-(3-pyridyl)-4-penten-2-ol (6.00 g, 36.81 mmol) in dry pyridine (30 mL) at 0° C. was added p-toluenesulfonyl chloride (21.05 g, 110.43 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 to give 11.67 g (84.0%) of a dark-brown, viscous oil.

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. customto give 11.67 g (84.0%) of a dark-brown, viscous oil

Sources & evidence

ORD record
ord-42e11a04f0334b2cba51fd27d8e01525
Source dataset
uspto-grants-2012_10
Patent number
US08288420B2

Reaction notes

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