Triethylamine → 2-Phenoxyethyl methanesulfonate

HRID 1466534

Reaktionsgleichung

Reaktionsgleichung von HRID 1466534
[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.O>[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]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31236PhenoxyethanolHCID 31297Methanesulfonyl chloride

Produkt 1

HCID 2264992-Phenoxyethyl methanesulfonateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-phenoxyethanol (10.0 mL, 80.0 mmol) and triethylamine (13.5 mL, 96.9 mmol) in anhydrous CH2Cl2 (250 mL) at 0° C. is added methanesulfonyl chloride (6.80 mL, 87.9 mmol). The resulting cloudy mixture is stirred at 0° C. for 2 h. The mixture is diluted with water (75 mL) and extracted. The organic layer is washed with 1N HCl (75 mL) then saturated NaHCO3/brine (1:1; 75 mL) dried (Na2SO4), filtered, and concentrated. The residue is dried to constant weight under reduced pressure to provide the title compound as a pale yellow oil (17.1 g, 99%). This material is used in the next step without further purification.

Aufarbeitung

  1. extractionextracted
  2. washThe organic layer is washed with 1N HCl (75 mL)
  3. dry with materialsaturated NaHCO3/brine (1:1; 75 mL) dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is dried to constant weight under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cffced9ee9e14d54820506abb6707b2f
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000043B2

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