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Cesium carbonate → 1-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinone

HRID 274941
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HRID 274941 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]2=[O:23])=[CH:4][C:3]=1[CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:34]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:35]([CH:34]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]2=[O:23])=[CH:4][C:3]=1[CH2:24][CH2:25][CH3:26])([O:37][CH2:38][CH3:39])=[O:36]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 15383768Ethyl alpha-bromo-3,4-methylenedioxyphenylacetateHCID 200891871-(4-Hydroxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

생성물 1

HCID 200891921-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinone수율 83%

시약·촉매·용매 2

HCID 311
Citric Acid
용매
HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 0.105 g (0.30 mmol) of the product of step C in 1.0 mL of DMF was added 0.115 g (0.33 mmol) of cesium carbonate and the resulting suspension was stirred under a nitrogen atmosphere for 15 minutes. A solution of 0.094 g (0.33 mmol) ethyl α-bromo-3,4-methylenedioxyphenylacetate in 0.5 mL of DMF was then added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then suspended in 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane; combination of the product fractions and evaporation in vacuo afforded 0.137 g (83%) of the title compound.

후처리

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on a silica gel flash chromatography column
  9. washeluted with 30% EtOAc-hexane
  10. customcombination of the product fractions and evaporation in vacuo

출처 및 근거

ORD 기록
ord-15778c484e1741f39a1e7ba002b98059
출처 데이터셋
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05391566

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