Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]- → HCID 178451083, Verbindung

HRID 271347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271347
[C:1]([O:5][C:6]([CH:8]=[C:9]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pt].C(O)C>[C:1]([O:5][C:6]([CH2:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 59834904Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 178451083HCID 178451083, VerbindungAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A mixture of 2 g of 3-tert-butoxycarbonylmethylene-cyclobutanecarboxylic acid, 150 mL of ethanol, 0.5 g of 5% platinum on carbon, and 200 mL of ethanol was stirred under 1 atm of hydrogen for 48 h overnight, filtered, diluted with 20 mL of toluene and concentrated under reduced pressure. Drying under vacuum overnight gave 2 g of product, which was predominantly as a colorless oil: 1H NMR (400 MHz, CDCl3) 10.2 (br s, 1H), 3.0 (m, 1H), 2.3 (m, 1H), 2.38 (m, 4H), 2.0 (dd, 2H), 1.4 (s, 9).

Aufarbeitung

  1. filtrationfiltered
  2. additiondiluted with 20 mL of toluene
  3. concentrationconcentrated under reduced pressure
  4. customDrying under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-95a0efb0825e4a77adb744b40e72c890
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452893B2

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