Hydrochloric Acid → 3-(6-Methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester

HRID 215829

反応式

HRID 215829 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[OH:10][C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+].Cl>N1C=CC=CC=1.[Cu]I>[CH2:17]([O:16][C:14](=[O:15])[C:13]1[CH:19]=[CH:20][CH:21]=[C:11]([O:10][C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[CH:12]=1)[CH3:18]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoateHCID 27348955-Bromo-2-methoxypyridine

生成物 1

HCID 672971443-(6-Methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester収率 23.6%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1049Pyridine溶媒

実験手順

A suspension of 5-bromo-2-methoxy-pyridine (5.4 g, 29 mmol), ethyl 3-hydroxybenzoate (4.0 g, 24 mmol), K2CO3 (4.3 g, 30 mmol), Cu powder (0.30 g, 4.8 mmol) and CuI (0.30 g, 1.56 mmol) in pyridine (25 ml) was refluxed for 18 h. The resulting mixture was mixed with 100 g of crushed ice, neutralized with 1N hydrochloric acid to pH 7.5 and extracted with ether. The extract was evaporated in vacuo, the obtained crude product was purified by column chromatography on silica (eluent hexanes-ethyl acetate 8:1) to afford 1.55 g (20%) of 3-(6-methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester as colorless oil.

後処理

  1. temperaturewas refluxed for 18 h
  2. extractionextracted with ether
  3. customThe extract was evaporated in vacuo
  4. customthe obtained crude product
  5. customwas purified by column chromatography on silica (eluent hexanes-ethyl acetate 8:1)

出典と根拠

ORDレコード
ord-44adbd6a96364be3b0f83d8ea7a0810e
出典データセット
uspto-grants-2012_06
特許番号
US08193192B2

関連ノート

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