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Cesium carbonate → 3-(6-Ethanesulfonyl-pyridin-3-yloxy)-5-methoxymethoxybenzoic acid methyl ester

HRID 2113825
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인쇄 미리보기

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HRID 2113825 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][C:21](=[O:33])[C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:24]([O:29][CH2:30][O:31][CH3:32])[CH:23]=1.[Cl-].[NH4+]>CN(C)C=O.C(OC(=O)C)C>[CH3:19][O:20][C:21](=[O:33])[C:22]1[CH:23]=[C:24]([O:29][CH2:30][O:31][CH3:32])[CH:25]=[C:26]([O:28][C:2]2[CH:7]=[N:6][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:27]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 225031645-Bromo-2-(ethylsulfonyl)pyridineHCID 23136427Methyl 3-hydroxy-5-(methoxymethoxy)benzoate

생성물 1

HCID 687119443-(6-Ethanesulfonyl-pyridin-3-yloxy)-5-methoxymethoxybenzoic acid methyl ester수율 92%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

After adding 178 mg (0.71 mmol) of 5-bromo-2-ethanesulfonylpyridine and 232 mg (0.71 mmol) of cesium carbonate to a solution of 100 mg (0.47 mmol) of 5-hydroxy-3-methoxymethoxybenzoic acid methyl ester in N,N-dimethylformamide (1.0 ml), the mixture was stirred at 100° C. for 2.5 hours under a nitrogen atmosphere. Acetic acid ethyl ester and aqueous ammonium chloride were added to the reaction mixture, the aqueous layer was extracted with acetic acid ethyl ester, and then the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=1:1) to obtain 165 mg of 3-(6-ethanesulfonyl-pyridin-3-yloxy)-5-methoxymethoxybenzoic acid methyl ester (yield: 91%) as a colorless oil.

후처리

  1. extractionthe aqueous layer was extracted with acetic acid ethyl ester
  2. washthe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=1:1)

출처 및 근거

ORD 기록
ord-d439aa5d93d943b7b577da576dac0baf
출처 데이터셋
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07432287B2

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