Phosphoric Acid → methyl 6-cyclohex-1-en-1-yl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505778ノート

反応式

HRID 505778 の反応式
[C:1]1([C:7]2[NH:11][C:10]3[CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[S:14][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(=O)C)(=O)C.[C:26]1(=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.P(=O)(O)(O)O>C(O)(=O)C>[C:26]1([C:8]2[C:9]3[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:10]=3[NH:11][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1

参加物

6

反応物 4

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 7967CyclohexanoneHCID 11492603methyl 5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

生成物 1

HCID 11559121methyl 6-cyclohex-1-en-1-yl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate収率 69%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

A solution (0.2 M) of methyl 5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in acetic acid was treated with acetic anhydride (10 eq.), cyclohexanone (10 eq.) and 85% phosphoric acid (2.3 eq.). The mixture was heated at 80° C. for 3 h, then was poured into ice cold ammonium hydroxide. The product was extracted with AcOEt and the combined organic layers were washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine then dried and concentrated. The crude was purified by flash chromatography on silica gel (1:4 AcOEt/petroleum ether) affording the title compound (69%) as a solid.

後処理

  1. additionwas poured into ice cold ammonium hydroxide
  2. extractionThe product was extracted with AcOEt
  3. washthe combined organic layers were washed sequentially with aqueous HCl (1 N), aqueous NaHCO3 (saturated solution) and brine
  4. customthen dried
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography on silica gel (1:4 AcOEt/petroleum ether)

出典と根拠

ORDレコード
ord-50908046b11849b491fd4af700b48971
出典データセット
uspto-grants-2010_08
特許番号
US07781431B2

反応ノート

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