반응 #1221

반응 방정식

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

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONOnce the addition
2. 2
   온도the mixture was heated
3. 3
   온도at reflux for one hour
4. 4
   온도the 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
   추출extracted with ethyl ether
8. 8
   기타the organic phase decanted off
9. 9
   건조dried over magnesium sulfate
10. 10
    기타evaporated
11. 11
    기타The residue obtained
12. 12
    기타was chromatographed on a silica column
13. 13
    세척eluted with a mixture of hexane and dichloromethane (60/40)
14. 14
    기타After evaporation of the solvents, 6.35 g (74%) of the expected ester of melting point 107°-108° C.
15. 15
    기타were recovered

실험 절차

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.

출처