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

HRID 1130

반응식

HRID 1130 반응식
[CH3:1][N:2]1[CH:6]=[C:5](I)[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9].[CH3:12][C:13]1([CH3:32])[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[C:23]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19](B(O)O)=[CH:20]3)=[CH:15][C:14]1=2.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:19]2[CH:18]=[CH:17][C:16]3[C:21](=[CH:22][C:23]4[C:24]([CH3:28])([CH3:27])[CH2:25][CH2:26][C:13]([CH3:32])([CH3:12])[C:14]=4[CH:15]=3)[CH:20]=2)[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 196946765,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acidHCID 21826247methyl 4-iodo-1-methyl-1H-pyrrole-2-carboxylate

생성물 1

HCID 19694675methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate수율 47%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. customThe reaction medium was evaporated to dryness
  4. customethyl ether, the organic phase decanted
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (80/20)

출처 및 근거

ORD 기록
ord-205c29c6463642c4a3ef2726db5ff6fc
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723499

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