4-Toluenesulfonyl chloride → HCID 87467528, compound

HRID 2064304Notes

Reaction equation

HRID 2064304 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[CH2:11][CH:12]([OH:14])[CH3:13])[CH:6]=[N:7][CH:8]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:14][CH:12]([CH2:11]/[CH:10]=[CH:9]/[C:5]2[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:13])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22060168HCID 22060168, compound

Product 1

HCID 87467528HCID 87467528, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (4E)-5-(5-methoxy-3-pyridyl)-4-penten-2-ol (3.50 g, 18.13 mmol) in dry pyridine (15 mL) at 0° C. was added p-toluenesulfonyl chloride (6.91 g, 36.27 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 5.25 g (83.5%) 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 5.25 g (83.5%) of a dark-brown, viscous oil

Sources & evidence

ORD record
ord-3f000b442d5245bebd0d0241d76456ea
Source dataset
uspto-grants-2012_10
Patent number
US08288420B2

Reaction notes

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