Triethylamine → Methyl [4-(3-methanesulfonyloxypropyl)phenoxy]acetate

HRID 1700945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700945
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)(=[O:27])=[O:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22949949Methyl [4-(3-hydroxypropyl)phenoxy]acetate

Produkt 1

HCID 22949950Methyl [4-(3-methanesulfonyloxypropyl)phenoxy]acetateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of methyl [4-(3-hydroxypropyl)phenoxy]acetate (4.5 g, 20.5 mmol) in dichloromethane (50 ml) was treated at 0° C. with triethylamine (4.36 g, 43.1 mmol) followed by methanesulfonyl chloride (3.99 g, 34.8 mmol) added dropwise over 5 min. After 30 min at 0° C., the reaction mixture was diluted with dichloromethane, washed with 1N hydrochloric acid, water and dried over anhydrous sodium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 8:18) gave 5.51 g (89%) of the title material as a white solid: mp 49-51° C.

Aufarbeitung

  1. additionadded dropwise over 5 min
  2. washwashed with 1N hydrochloric acid, water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 8:18)

Quellen und Nachweise

ORD-Eintrag
ord-3738c5ec6158472393c6b0833dd9c065
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350892B1

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