Reaktion #1072783

Reaktionsgleichung

sodium hydrogen carbonate

water ethyl acetate

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

hydrochloric acid

→

title compound

Ausbeute 98.0%

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

Ausbeute 98.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux for 2.5 hours under nitrogen atmosphere
3. 3
   Extraktionextracted three times with ethyl acetate
4. 4
   Waschenwashed with water and saturated brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of 2,3,6,7-tetrahydro-2-(iodomethyl)-2,4,6,6,8-pentamethyl-5H-furo[2,3-f]indole-5-carbaldehyde (2.42 g, 6.06 mmol) in methanol (10 ml) was added concentrated hydrochloric acid (3 ml), and heated under reflux for 2.5 hours under nitrogen atmosphere. The reaction mixture was added dropwise to a mixture of sodium hydrogen carbonate (3.7 g, 44 mmol) with water-ethyl acetate, neutralized and extracted three times with ethyl acetate. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain 2.20 g of the title compound.

Quelle