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Dimethylformamide → 2-carbopropoxy-6-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H1-benzopyran

HRID 1090779
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인쇄 미리보기

반응식

HRID 1090779 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[C:21]([C:27]1[O:28][C:29]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][C:30]=2[C:31](=[O:33])[CH:32]=1)([O:23][CH2:24][CH2:25][CH3:26])=[O:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(C)=O>[C:21]([C:27]1[O:28][C:29]2[CH:37]=[CH:36][C:35]([O:38][CH2:2][C:3]3[CH:20]=[CH:19][CH:18]=[C:5]([O:6][CH2:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)[CH:4]=3)=[CH:34][C:30]=2[C:31](=[O:33])[CH:32]=1)([O:23][CH2:24][CH2:25][CH3:26])=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 199138472-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran

생성물 1

HCID 199138482-carbopropoxy-6-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H1-benzopyran수율 28.2%

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

A mixture of 3.47g of 2-((3-chloromethylphenoxy)methyl)quinoline, 3.04g of 2-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran, 1.69g of potassium carbonate and 1 ml of dimethylformamide is refluxed in 50 ml of acetone for 41 hours. The mixture is concentrated in vacuo and the residue is dissolved in water. This solution is neutralized with diluted hydrochloric acid and the resulting solid is filtered off and purified by flash silica gel chromatography in propanol-dimethylformamide to give 1.71 g of 2-carbopropoxy-6-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran as a white solid having an m.p. of 109°-10° C.

후처리

  1. concentrationThe mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in water
  3. filtrationthe resulting solid is filtered off
  4. custompurified by flash silica gel chromatography in propanol-dimethylformamide

출처 및 근거

ORD 기록
ord-e4271e3addaf4b8d83c36d91afe706c0
출처 데이터셋
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05082849

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