Ethyl bromoacetate → 4-(3-Pyridylmethyl)phenoxyacetic acid ethyl ester

HRID 1680031노트

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HRID 1680031 반응식
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[H-].[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)=[CH:10][CH:11]=1)[CH3:24]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 132901364-(3-Pyridylmethyl)phenol hydrochloride

생성물 1

HCID 544292054-(3-Pyridylmethyl)phenoxyacetic acid ethyl ester수율 19.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 0.70 g of the phenol compound (prepared as described in Example 9), 0.30 g of sodium hydride (content 63%) and 14 ml of N, N-dimethylformamide was stirred at 100° C. for 20 minutes, and stirred with 0.64 g of ethyl bromoacetate at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water, and extracted with diethyl ether. The extract was washed with water, and a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a 0.5% V/V solution of ethanol in chloroform as eluent to give 0.166 g of the title compound having the following physical characteristics:

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using a 0.5% V/V solution of ethanol in chloroform as eluent

출처 및 근거

ORD 기록
ord-35306f858dae4529927e9e023bb33a92
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04271170

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