Reaktion #1072779

Reaktionsgleichung

2,3-Dihydro-5-hydroxy-4,7-dimethyl-6-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde

calcium carbonate

trimethylammonium dichloroiodate

→

title compound

Ausbeute 88.0%

3,5,6,7-Tetrahydro-2-(iodomethyl)-2,4,8-trimethyl-2H-furo[2,3-f]indole-5-carbaldehyde

Ausbeute 88.0%

Lösungsmittel

methanol THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe reaction mixture was filtered
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with water and saturated brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   Sonstigethe solvent was removed under reduced pressure
7. 7
   SonstigeThe residue was crystallized from ethyl acetate-hexane

Vorschrift

2,3-Dihydro-5-hydroxy-4,7-dimethyl-6-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (4.17 g, 17.0 mmol) was dissolved in methanol-THF solution (34 ml, 1:1). To the mixture was added calcium carbonate (2.21 g, 22.1 mmol) and then trimethylammonium dichloroiodate (6.51 g, 18.7 mmol) was added. After stirring for 1 hour at room temperature, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was combined a 10% aqueous solution of sodium thiosulfate, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain 5.52 g of the title compound.

Quelle