Water → methyl 4-iodo-1-methyl-1H-pyrrole-2-carboxylate

HRID 1129

반응식

HRID 1129 반응식
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:7][CH:8]=1.I[CH3:14].O>CN(C=O)C>[CH3:14][N:7]1[CH:8]=[C:4]([I:3])[CH:5]=[C:6]1[C:9]([O:11][CH3:12])=[O:10]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11673249methyl 4-iodo-1H-pyrrole-2-carboxylate

생성물 1

HCID 21826247methyl 4-iodo-1-methyl-1H-pyrrole-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

780 mg (25.9 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 6.5 g (25.9 mmol) of methyl 4-iodo-2-pyrrolecarboxylate in 50 ml of DMF was added dropwise and the mixture was stirred until gaseous emission ceased. 2.1 ml (33.6 mmol) of iodomethane were then added and the mixture was stirred at room temperature for two hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (40/60). 4.5 g (65%) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate of melting point 64°-65° C. were recovered.

후처리

  1. stirringthe mixture was stirred at room temperature for two hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase decanted
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (40/60)
  9. custom4.5 g (65%) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate of melting point 64°-65° C. were recovered

출처 및 근거

ORD 기록
ord-8254c501c8dc491b8f88eae119f49eae
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723499

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