4-Toluenesulfonyl chloride → 2-(Pyridin-3-yl)ethyl 4-methylbenzene-1-sulfonate

HRID 633751Notes

Reaction equation

HRID 633751 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][OH:27])[CH:20]=1>ClCCl>[C:9]1([CH3:8])[CH:14]=[CH:13][C:12]([S:15]([O:27][CH2:26][CH2:25][C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 805153-Pyridineethanol

Product 1

HCID 865973652-(Pyridin-3-yl)ethyl 4-methylbenzene-1-sulfonateYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.62 mL (47.26 mmol) of triethylamine and 8.26 g (43.32 mmol) of 4-methylbenzenesulfonyl chloride are added at 0° C. to a solution of 5 g (39.38 mmol) of 2-pyrid-3-ylethanol in 300 mL of dichloromethane. After allowing the reaction medium to warm to room temperature and stirring overnight, it is washed with water and with saturated NaCl solution. The organic phase is dried over magnesium sulfate and evaporated to dryness. After purification by chromatography on silica gel (eluent: 4/6 heptane/EtOAc), 8 g of 2-pyrid-3-ylethyl toluene-4-sulfonate were obtained, corresponding to the following characteristics:

Workup

  1. washit is washed with water and with saturated NaCl solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated to dryness
  4. customAfter purification by chromatography on silica gel (eluent: 4/6 heptane/EtOAc)

Sources & evidence

ORD record
ord-5f628e2afad841388b4fdb6f637f4f0e
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

Loading…