Réaction #1221

Équation de réaction

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-bromoanthracene

magnesium

ethyl 2-bromo-4-thiophenecarboxylate

→

ethyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-4-thiophenecarboxylate

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONOnce the addition
2. 2
   Températurethe mixture was heated
3. 3
   Températureat reflux for one hour
4. 4
   Températurethe mixture was maintained
5. 5
   workup.STIRRINGunder stirring at room temperature for 12 hours
6. 6
   workup.ADDITIONThe reaction medium was poured into ice-cold water
7. 7
   Extractionextracted with ethyl ether
8. 8
   Autrethe organic phase decanted off
9. 9
   Séchagedried over magnesium sulfate
10. 10
    Autreevaporated
11. 11
    AutreThe residue obtained
12. 12
    Autrewas chromatographed on a silica column
13. 13
    Lavageeluted with a mixture of hexane and dichloromethane (60/40)
14. 14
    AutreAfter evaporation of the solvents, 6.35 g (74%) of the expected ester of melting point 107°-108° C.
15. 15
    Autrewere recovered

Mode opératoire

A solution of 9.5 g (30 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-bromoanthracene was added dropwise to a suspension of 724 mg (30 mmol) of magnesium in 10 ml of THF. Once the addition was completed, the mixture was heated at reflux for one hour. At room temperature 4.1 g (30 mmol) of anhydrous zinc chloride were added and the mixture was stirred for one hour. 5.2 g (22 mmol) of ethyl 2-bromo-4-thiophenecarboxylate and 120 mg (0.22 mmol) of the complex NiCl2 /DPPE were then added successively and the mixture was maintained under stirring at room temperature for 12 hours. The reaction medium was poured into ice-cold water, extracted with ethyl ether, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue obtained was chromatographed on a silica column eluted with a mixture of hexane and dichloromethane (60/40). After evaporation of the solvents, 6.35 g (74%) of the expected ester of melting point 107°-108° C. were recovered.

Source