4-Toluenesulfonyl chloride → 2-(6-Methoxypyridin-2-yl)ethyl 4-methylbenzenesulfonate

HRID 535667

Reaction equation

HRID 535667 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:11][CH2:10][CH2:9][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 153198712-(6-Methoxypyridin-2-yl)ethan-1-ol

Product 1

HCID 596367762-(6-Methoxypyridin-2-yl)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(6-methoxypyridin-2-yl)ethanol (0.23 g, 1.50 mmol), 4-dimethylaminopyridine (0.028 g, 0.23 mmol), triethylamine (0.63 mL, 4.50 mmol) and p-toluenesulfonyl chloride (0.34 g, 1.80 mmol) in dry dichloromethane (5 mL) was stirred at rt over night. The solvent was removed in vacuo. Ethyl acetate and water were added. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried (Na2SO4) and concentrated. The product was purified by flash chromatography (SiO2; heptane/EtOAc, gradient 0-100%). Yield: 0.18 g (38%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionEthyl acetate and water were added
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (SiO2; heptane/EtOAc, gradient 0-100%)

Sources & evidence

ORD record
ord-70334fdf56194307bd8210e70a762595
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Linked notes

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