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

HRID 861777

반응식

HRID 861777 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 stirring was carried out until gas evolution has ceased. 2.1 ml (33.6 mmol) of iodomethane were then added and stirring was carried out at room temperature for two hours. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and was 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, with a melting point of 64°-65° C., were recovered.

후처리

  1. stirringstirring
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customwas evaporated
  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, with a melting point of 64°-65° C., were recovered

출처 및 근거

ORD 기록
ord-31aeb1bc853e41d29c7e79ed8f8d59ef
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716624

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