Reaktion #5765

Reaktionsgleichung

hexane

ethyl acetate

3,7,11-trimethyl-12-(methoxymethyl)oxy-1,6,10-dodecatrien-3-ol

pyridinium chlorochromate

→

12-(methoxymethyl)oxy-3,7,11-trimethyl-2,6,10-dodecatrienal

Ausbeute 52.0%

Lösungsmittel

ether

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   Filtrationinsoluble materials were filtered
3. 3
   EinengenThe filtrate was concentrated in vacuo
4. 4
   Sonstigethe residue was purified with silica gel column chromatography

Vorschrift

A solution of 3,7,11-trimethyl-12-(methoxymethyl)oxy-1,6,10-dodecatrien-3-ol (460 mg, 1.6 mmol) in dichloromethane (30 ml) was added pyridinium chlorochromate (690 mg, 3.2 mmol), and the mixture was stirred at room temperature for 8 hours. After addition of a mixture of hexane, ethyl acetate, and ether (3:1:1) (100 ml), the mixture was stirred and insoluble materials were filtered. The filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography to give 12-(methoxymethyl)oxy-3,7,11-trimethyl-2,6,10-dodecatrienal (233 mg, 52%). The physico-chemical properties of the product was the same as those described in Reference Example 1.

Quelle