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

HRID 505778노트

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HRID 505778 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-50908046b11849b491fd4af700b48971
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781431B2

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