Triethylamine → 2-Phenoxyethyl methanesulfonate

HRID 5465

Reaction equation

HRID 5465 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][S:19]([O:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31236PhenoxyethanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 2264992-Phenoxyethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(phenoxy)ethanol (1.35 g, 9.78 mmoles) and triethylamine (2.04 ml, 14.7 mmoles) in methylene chloride (30 ml) was added methanesulfonyl chloride (0.91 ml, 12 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 10 minutes. The reaction solution was washed with water and the aqueous layer was extracted with methylene chloride (30 ml×3). The methylene chloride layers were combined and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was subjected to column chromatography [eluent: hexane/methyl (1:1)] to obtain crude 1-methanesulfonyloxy-2-(phenoxy)ethane as a pale yellow oily product.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred under ice-
  3. temperaturecooling for 10 minutes
  4. washThe reaction solution was washed with water
  5. extractionthe aqueous layer was extracted with methylene chloride (30 ml×3)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-eb8851427b2141259138fbc58018c19f
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

Loading…