4-Toluenesulfonyl chloride → HCID 11076628, compound

HRID 1422569Notes

Reaction equation

HRID 1422569 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:16]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8134Diethylene Glycol Monomethyl EtherHCID 8471Triethylamine

Product 1

HCID 11076628HCID 11076628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2-methoxyethoxy)ethanol (200 mg, 1.67 mmol, 1 equiv.), triethylamine (232 μL, 1.67 mmol, 1.0 equiv.) and tosyl chloride (317 mg, 1.67 mmol, 1 equiv.) in methylene chloride (5 mL, 0.29 M) was stirred at room temperature for 50 hours. After removal of the solvent under reduced pressure, the residue was purified by chromatography on silica gel (10 g, hexanes/EtOAc 9:1 to 1:1) to afford (2-methoxyethoxy)ethyl 4-methylbenzenesulfonate as a colorless oil (260 mg, 457 mg theoretical, 56.9%). LC-MS m/z 275 (M+1).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (10 g, hexanes/EtOAc 9:1 to 1:1)

Sources & evidence

ORD record
ord-99dd72a342514f5383b6e4b3aeb20b5a
Source dataset
uspto-grants-2015_01
Patent number
US08927525B2

Reaction notes

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