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

HRID 1363266ノート

反応式

HRID 1363266 の反応式
[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

参加物

4

反応物 2

HCID 167693Trimethylsilyldiazomethane2 回HCID 49612544H-thieno(3,2-b)pyrrole-5-carboxylic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-639a84915ca14e369ce8dc4aaed361e0
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

反応ノート

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