Reaktion #1376326

Reaktionsgleichung

8-bromo-THTMDBF

8-bromo-1,2,3,4-tetrahydro-1,4a,9b-trimethyl-1,4-methanodibenzofuran

magnesium

iodine

tetrahydrofuran

→

expected compound

Ausbeute 74.0%

1,2,3,4-Tetrahydro-1,4a,9b-trimethyl-1,4methanodibenzofuran-8-carbaldehyde

Ausbeute 74.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 2 h, 30 min
2. 2
   FiltrationAfter the magnesium was filtered off
3. 3
   workup.ADDITIONthe reaction medium was poured into ice-cold water
4. 4
   Extraktionextracted with ether
5. 5
   WaschenThe organic phase was washed with water
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated

Vorschrift

13.76 g (44.8 mmol) of 8-bromo-THTMDBF obtained in Example 2 were added dropwise into a three-necked flask under nitrogen containing 1.31 g of magnesium and an iodine crystal in 5 ml of tetrahydrofuran, and the mixture was maintained under reflux for 2 h, 30 min. After the magnesium was filtered off, the reaction medium was poured into ice-cold water, acidified to pH 1 with concentrated hydrochloric acid and extracted with ether. The organic phase was washed with water, dried over magnesium sulfate, filtered and evaporated to yield 8.47 g (74%) of the expected compound, melting at 144.7° C.; αD =-7° (c=1, chloroform).

Quelle