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

HRID 1431936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431936
[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].[CH3:14][C:15]1C=CC(S(O)(=O)=O)=C[CH:20]=1>COC(OC)(C)C.C(Cl)Cl>[CH3:14][C:15]1([CH3:20])[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 B-4 (300 mg, 1.58 mmol) in 2,2-dimethoxypropane (10 mL) is added p-TSA (20 mg) and the reaction is stirred at rt for 16 hours. The solution is diluted with DCM 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 B-5.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-aac7c92818d24f2fadbda2a899388737
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612059B2

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