p-Toluenesulfonic acid → 2-(2,2-Dimethyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid

HRID 1008281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1008281
[CH2:1]([C@@H:5]([C:11]([OH:13])=[O:12])[C@H:6]([OH:10])[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH3:4].[C:14]1(C)[CH:19]=CC(S(O)(=O)=O)=C[CH:15]=1>COC(OC)(C)C.ClCCl>[CH3:15][C:14]1([CH3:19])[O:8][C:7](=[O:9])[CH:6]([CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:11]([OH:13])=[O:12])[O:10]1

Komponenten

5

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 60111363(2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid

Produkt 1

HCID 222565262-(2,2-Dimethyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 64952,2-DimethoxypropaneLösungsmittel

Versuchsvorschrift

To a solution of (2S, 3R)-3-(n-butyl)-2-hydroxysuccinic acid F-4 (300 mg, 1.58 mmol) in 2,2-dimethoxypropane (10 mL) was added p-toluenesulfonic acid (20 mg) and the reaction was stirred at room temperature for 16 h. The solution was diluted with dichloromethane and washed with brine, dried (Na2SO4) and then purified by silica gel chromatography to afford 1.2 mmol 2-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid F-5 (78%).

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e9e5b84286444fde9e5e254400c0bfa4
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797820B2

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