Triethylamine → Methanesulfonyloxy(4-methanesulfonyloxyphenyl)-acetic acid methyl ester

HRID 2306617

Reaktionsgleichung

Reaktionsgleichung von HRID 2306617
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]1[CH:19]=[CH:18][C:10]([CH:11]([OH:17])[C:12]([O:14][CH2:15]C)=[O:13])=[CH:9][CH:8]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:15][O:14][C:12](=[O:13])[CH:11]([O:17][S:2]([CH3:1])(=[O:4])=[O:3])[C:10]1[CH:18]=[CH:19][C:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111357Benzeneacetic acid, alpha,4-dihydroxy-, ethyl ester

Produkt 1

HCID 88018735Methanesulfonyloxy(4-methanesulfonyloxyphenyl)-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (0.395 ml, 5.10 mmol) is added dropwise at 0° C. to ethyl 4-hydroxymandelate (0.500 g, 2.55 mmol) and triethylamine (0.889 ml, 6.38 mmol) in DMF (5 ml) and the mixture is allowed to warm to room temperature overnight. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried (MgSO4), and evaporated to give oily residue which is purified by flash column chromatography (30% EtOAc/Hexane) (0.75 g, 82%). MS (m/z): [M+H]+=353.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give oily residue which
  6. customis purified by flash column chromatography (30% EtOAc/Hexane) (0.75 g, 82%)

Quellen und Nachweise

ORD-Eintrag
ord-0f02e586205a4cb9b87e93177351fb27
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06828317B2

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