p-Toluenesulfonic acid → (1R,4R,5S) 4-[dihydro-2-oxo-3-(2H)-thienyl]-6,6-dimethyl-3-oxabicyclo-(3,1,0)-hexan-2-one

HRID 648366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648366
C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:12]=[C:13]1[CH:17]([CH:18]([OH:27])[C@H:19]2[C@@H:21]([C:22]([OH:24])=O)[C:20]2([CH3:26])[CH3:25])[CH2:16][CH2:15][S:14]1>C1C=CC=CC=1>[O:12]=[C:13]1[CH:17]([C@H:18]2[C@H:19]3[C@H:21]([C:20]3([CH3:25])[CH3:26])[C:22](=[O:24])[O:27]2)[CH2:16][CH2:15][S:14]1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 70534022(1R,3S) 3[(dihydro-2-oxo-3(2H)-thienyl)-hydroxymethyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid

Produkt 1

HCID 22824566(1R,4R,5S) 4-[dihydro-2-oxo-3-(2H)-thienyl]-6,6-dimethyl-3-oxabicyclo-(3,1,0)-hexan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

50 mg of p-toluene sulfonic acid were added to a solution of 6.2 g of the product of Step A in 70 ml of benzene and the mixture was refluxed for 90 minutes while removing the water of reaction by passing the condensed solvent through silica gel to obtain a solution of (1R,4R,5S) 4-[dihydro-2-oxo-3-(2H)-thienyl]-6,6-dimethyl-3-oxabicyclo-(3,1,0)-hexan-2-one which was used as is for the next step.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customwhile removing
  3. customthe water of reaction

Quellen und Nachweise

ORD-Eintrag
ord-18edd09d14fe41349a5002b082b1a115
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04412069

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