Dimethylformamide → Ethyl 2-bromo-6-formyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 928531ノート

反応式

HRID 928531 の反応式
O=P(Cl)(Cl)Cl.[Br:6][C:7]1[S:14][C:13]2[CH:12]=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:10][C:9]=2[CH:8]=1.CN([CH:23]=[O:24])C>>[Br:6][C:7]1[S:14][C:13]2[C:12]([CH:23]=[O:24])=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:10][C:9]=2[CH:8]=1

参加物

4

反応物 3

HCID 6228Dimethylformamide2 回HCID 24813Phosphorus oxychlorideHCID 13164349ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

生成物 1

HCID 58386865Ethyl 2-bromo-6-formyl-4H-thieno[3,2-b]pyrrole-5-carboxylate収率 75%

実験手順

To DMF (2.05 mL) cooled by ice/water was added POCl3 dropwise and the mixture was stirred for 30 min. A solution of carboxylate 61 (1.96 g, 7.15 mmol) in DMF (2.5 mL) was added at this temperature and the mixture was allowed to warm to room temperature then heated to 60° C. After 16 h, the reaction mixture was cooled to room temperature. and poured into ice/water. The mixture was extracted with EtOAc (3×20 mL) and the combined organic layers were washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4. After removed the organic solvent, the residue was purified by column chromatography (EtOAc/Hexane: 1/4) to give the desired aldehyde 62 (1.62 g, 75%) as a white solid.

後処理

  1. temperaturethen heated to 60° C
  2. waitAfter 16 h
  3. temperaturethe reaction mixture was cooled to room temperature
  4. extractionThe mixture was extracted with EtOAc (3×20 mL)
  5. washthe combined organic layers were washed with aqueous saturated NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. customAfter removed the organic solvent
  8. customthe residue was purified by column chromatography (EtOAc/Hexane: 1/4)

出典と根拠

ORDレコード
ord-f39b8e42a8e646a5954ea2bf21bf799a
出典データセット
uspto-grants-2016_03
特許番号
US09290512B2

反応ノート

読み込み中…