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

HRID 2113825
ノート
印刷プレビュー

反応式

HRID 2113825 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d439aa5d93d943b7b577da576dac0baf
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07432287B2

反応ノート

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