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

HRID 505825
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HRID 505825 반응식
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]2[CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[S:21][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[C:33]1(=O)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.P(=O)(O)(O)O>C(O)(=O)C>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)[C:10]2[CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[S:21][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 7967CyclohexanoneHCID 68471240methyl 6-benzyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

생성물 1

HCID 68467568methyl 6-benzyl-4-cyclohex-1-en-1-yl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate수율 95%

시약·촉매·용매 1

HCID 176
Acetic Acid
용매

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온도
80 °C

실험 절차

A solution (0.2 M) of methyl 6-benzyl-5-phenyl-6H-thieno[2,3-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 phase was 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 (1:30 acetone/toluene) affording the title compound (95%) as a solid.

후처리

  1. additionwas poured into ice cold ammonium hydroxide
  2. extractionThe product was extracted with AcOEt
  3. washthe combined organic phase was 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 (1:30 acetone/toluene)

출처 및 근거

ORD 기록
ord-95b360f9a3c646b79a7df11c424211a8
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07781431B2

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