反応 #1226

反応方程式

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid

potassium carbonate

methyl N-methyl-4-iodo-2-pyrrolecarboxylate

→

methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate

収率 47.0%

溶媒

toluene

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度at reflux for 8 hours
3. 3
   その他The reaction medium was evaporated to dryness
4. 4
   その他ethyl ether, the organic phase decanted
5. 5
   乾燥dried over magnesium sulfate
6. 6
   その他evaporated
7. 7
   その他The residue was purified by chromatography on a silica column
8. 8
   洗浄eluted with a mixture of dichloromethane and hexane (80/20)

実験手順

231 mg (0.2 mml) of tetrakis-(triphenylphosphine)palladium (0), 50 ml of toluene and 1.75 g (6.6 mmol) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate were introduced into a three-necked flask and under a nitrogen stream and the mixture was stirred at room temperature for 20 minutes. 2.8 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid and 6.6 ml of an aqueous potassium carbonate solution (2N) were then added and the mixture was heated at reflux for 8 hours. The reaction medium was evaporated to dryness, taken up in water and ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (80/20). 840 mg (47%) of methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate were obtained.

出典