反応 #1221

反応方程式

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

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONOnce the addition
2. 2
   温度the mixture was heated
3. 3
   温度at reflux for one hour
4. 4
   温度the 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
   抽出extracted with ethyl ether
8. 8
   その他the organic phase decanted off
9. 9
   乾燥dried over magnesium sulfate
10. 10
    その他evaporated
11. 11
    その他The residue obtained
12. 12
    その他was chromatographed on a silica column
13. 13
    洗浄eluted with a mixture of hexane and dichloromethane (60/40)
14. 14
    その他After evaporation of the solvents, 6.35 g (74%) of the expected ester of melting point 107°-108° C.
15. 15
    その他were recovered

実験手順

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.

出典