4-Toluenesulfonyl chloride → HCID 11076628, compound

HRID 2194959Notes

Reaction equation

HRID 2194959 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(Cl)Cl.C(N(CC)CC)C>[S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:11])=[O:10]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8134Diethylene Glycol Monomethyl EtherHCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate

Product 1

HCID 11076628HCID 11076628, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-(2-methoxyethoxy)ethanol 3.06 g (25.6 mmol) and TsCl 6.25 g (32.78 mmol) were dissolved in freshly distilled CH2Cl2, triethylamine (7.1 mL) was added then stirred under argon overnight. Saturated sodium bicarbonate solution (40 mL) and ethyl acetate (100 ml) were added. The organic layer was washed with 1N potassium bisulfate (80 mL), then saturated sodium bicarbonate solution (80 mL), dried over Na2SO4, then dried on rotavap to produce an oil. The product was purified on silica gel flash column with CHCl3:EtOAc=5:1. Product (8) 6.77 g (97% yield) was obtained as a colorless oil. Solvents such as CH3CN and THF may be used instead of CH2Cl2 in the synthesis of compound 8.

Workup

  1. additionwas added
  2. washThe organic layer was washed with 1N potassium bisulfate (80 mL)
  3. dry with materialsaturated sodium bicarbonate solution (80 mL), dried over Na2SO4
  4. customdried on rotavap
  5. customto produce an oil
  6. customThe product was purified on silica gel flash column with CHCl3

Sources & evidence

ORD record
ord-524fdad98a4349788186b993d7d8efe9
Source dataset
uspto-grants-2012_12
Patent number
US08334377B2

Reaction notes

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