4-Toluenesulfonyl chloride → (2R)-(4E)-5-(5-isopropoxy-3-pyridyl)4-penten-2-ol p-toluenesulfonate

HRID 968406Notes

Reaction equation

HRID 968406 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:11]=[CH:12]/[CH2:13][C@H:14]([OH:16])[CH3:15])[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:2].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:16][C@@H:14]([CH2:13]/[CH:12]=[CH:11]/[C:7]2[CH:8]=[N:9][CH:10]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=2)[CH3:15])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12052266(2R)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol

Product 1

HCID 12052269(2R)-(4E)-5-(5-isopropoxy-3-pyridyl)4-penten-2-ol p-toluenesulfonateYield 81.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (2R)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol (8.50 g, 38.46 mmol) in dry pyridine (30 mL) at 0° C. was added p-toluenesulfonyl chloride (14.67 g, 76.92 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 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 yield a dark-brown, viscous oil (11.75 g, 81.5%).

Workup

  1. customThe pyridine was removed by rotary evaporation
  2. additionToluene (50 mL) was added to the residue
  3. customremoved 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

Sources & evidence

ORD record
ord-ba63ed5371e84530ab9c745eb0bd9a8c
Source dataset
uspto-grants-2005_10
Patent number
US06958399B2

Reaction notes

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