Trimethylsilyldiazomethane → methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 1363266

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HRID 1363266 반응식
[S:1]1[C:8]2[CH:7]=[C:6]([C:9]([OH:11])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.[CH3:12][Si](C=[N+]=[N-])(C)C>CO>[S:1]1[C:8]2[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1

참가 물질

4

반응물 2

HCID 167693Trimethylsilyldiazomethane2회HCID 49612544H-thieno(3,2-b)pyrrole-5-carboxylic acid

생성물 1

HCID 4058811methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate수율 86%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

4H-thieno[3,2-b]pyrrole-5-carboxylic acid (3.0 g, 17.9 mmol) was dissolved in anhydrous MeOH (50.0 mL) and cooled to 0° C. A solution (45.0 mL, 2 M in hexanes) of trimethylsilyldiazomethane (45 mL) was added in portions and the yellow color of the TMSCH2N2 remained. Stirring was continued for 10 min and then the excess TMSCH2N2 was quenched with acetic acid (5.0 mL). The solvent was removed with N2 stream, and the residue was chromatographed over silica gel (5%-40%, 30 min, EtOAc in heptane) to give methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (2.8 g, 86% yield). 1H NMR (400 MHz, CD3Cl) δ ppm 3.90 (s, 3H) 6.95 (dd, J=5.32, 0.78 Hz, 1H) 7.13 (dd, J=1.88, 0.76 Hz, 1H) 7.33 (d, J=5.37 Hz, 1H) 9.02 (br. s, 1H).

후처리

  1. customthe excess TMSCH2N2 was quenched with acetic acid (5.0 mL)
  2. customThe solvent was removed with N2 stream
  3. customthe residue was chromatographed over silica gel (5%-40%, 30 min, EtOAc in heptane)

출처 및 근거

ORD 기록
ord-639a84915ca14e369ce8dc4aaed361e0
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884124B2

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