Diketene → HCID 21932485, Verbindung

HRID 1870703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870703
[CH3:1][CH:2]([CH:10]=[CH2:11])[CH2:3][CH2:4][CH2:5][C:6]([OH:9])([CH3:8])[CH3:7].[CH2:12]=[C:13]1[O:17][C:15](=[O:16])[CH2:14]1>CN(C)C1C=CN=CC=1>[O:17]=[C:13]([CH3:12])[CH2:14][C:15]([O:9][C:6]([CH3:7])([CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH:10]=[CH2:11])[CH3:8])=[O:16]

Komponenten

4

Edukt 2

HCID 12661DiketeneHCID 29096Dihydromyrcenol

Produkt 1

HCID 21932485HCID 21932485, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of dihydromyrcenol (37.88 g, 0.240 mol) and 4-dimethylaminopyridine (0.16 g, 1.30 mmol) in a 100 mL three-necked round-bottomed flask fitted with a condenser, argon inlet, addition funnel, magnetic stirrer and internal thermometer is heated to 50-60° C. Diketene (20.16 g, 0.240 mol) is added dropwise in the course of 15 min. The mixture has a slight exotherm and turned from yellow to red during this time. After stirring an additional hour at 50° C., the mixture is cooled to room temperature. At this point, NMR analysis indicates the reaction is complete. Purification of the product mixture by flash chromatography (elution with dichloromethane) yields the desired product in 95% yield as a nearly colorless oil.

Aufarbeitung

  1. customfitted with a condenser, argon inlet, addition funnel, magnetic stirrer
  2. temperaturethe mixture is cooled to room temperature
  3. customPurification of the product mixture
  4. washby flash chromatography (elution with dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-7ac4e1edabfc46c78067f1dc5735bd8c
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06100233

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