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

HRID 215829노트

반응식

HRID 215829 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-44adbd6a96364be3b0f83d8ea7a0810e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193192B2

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