Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]- → cis-3-tert-Butoxycarbonylmethyl-cyclobutanecarboxylic acid

HRID 2202270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202270
[C:1]([O:5][C:6](=[O:15])[CH:7]=[C:8]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6](=[O:15])[CH2:7][CH:8]1[CH2:9][CH:10]([C:12]([OH:14])=[O:13])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 59834874cis-3-tert-Butoxycarbonylmethyl-cyclobutanecarboxylic acidAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(2-(tert-butoxy)-2-oxoethylidene)cyclobutanecarboxylic acid (3.4 g, 16.02 mmol) and 10% palladium-carbon (100 mg, 0.94 mmol, 50%, wet) in MeOH (30 mL) was stirred at room temperature for 5 hr under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 30→100% ethyl acetate/hexane) to give 3-(2-(tert-butoxy)-2-oxoethyl)cyclobutanecarboxylic acid (3.40 g, 15.87 mmol, 99%) as a colorless oil.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 30→100% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ef0fe15b66f842709d0e4b747a64ad93
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365520B2

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