4-Toluenesulfonyl chloride → HCID 87466225, compound

HRID 1711518Notes

Reaction equation

HRID 1711518 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:12]([O:15][C:16]1[CH:17]=[C:18](/[CH:22]=[CH:23]/[CH2:24][C@@H:25]([OH:27])[CH3:26])[CH:19]=[N:20][CH:21]=1)([CH3:14])[CH3:13]>C(N(CC)CC)C>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:27][C@H:25]([CH2:24]/[CH:23]=[CH:22]/[C:18]2[CH:19]=[N:20][CH:21]=[C:16]([O:15][CH:12]([CH3:14])[CH3:13])[CH:17]=2)[CH3:26])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68477280(2S)-(4E)-5-(5-Isopropoxy-3-pyridyl)-4-penten-2-ol

Product 1

HCID 87466225HCID 87466225, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, p-toluenesulfonyl chloride (11.45 g, 60.06 mmol) was added to a stirring solution of (2S)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol (7.00 g, 31.63 mmol) in dry triethylamine (30 mL) at 0° C. After stirring and warming to ambient temperature over 18 h, the mixture was concentrated on a rotary evaporator. The crude product was stirred with saturated NaHCO3 solution (100 mL) for 1 hour and extracted with chloroform (3×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation to afford 10.00 g (84.2%) as a dark-brown oil, which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated on a rotary evaporator
  2. stirringThe crude product was stirred with saturated NaHCO3 solution (100 mL) for 1 hour
  3. extractionextracted with chloroform (3×50 mL)
  4. dry with materialThe combined chloroform extracts were dried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customto afford 10.00 g (84.2%) as a dark-brown oil, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-c0d9e37ab4aa46e692bd43a334e160f3
Source dataset
uspto-grants-2010_09
Patent number
US07790757B2

Reaction notes

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