Phenol → Ethyl 6-chloro-4-phenoxynicotinate

HRID 1358617노트

반응식

HRID 1358617 반응식
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13](=[O:22])[C:14]1[C:19](Cl)=[CH:18][C:17]([Cl:21])=[N:16][CH:15]=1)[CH3:11]>CN(C)C=O>[CH2:10]([O:12][C:13](=[O:22])[C:14]1[C:19]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:18][C:17]([Cl:21])=[N:16][CH:15]=1)[CH3:11]

참가 물질

5

반응물 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

생성물 1

HCID 54487232Ethyl 6-chloro-4-phenoxynicotinate수율 70.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a solution of 196 mg (ca. 4 mmol) sodium hydride dispersion in mineral oil (ca. 50%) in 15 ml N,N-dimethylformamide a solution of 385 mg (4.09 mmol) phenol in 10 ml N,N-dimethylformamide was added dropwise at room temperature under argon. After 15 min. this solution was slowly added via cannula to a solution of 4,6-dichloro-nicotinic acid ethyl ester in 20 ml N,N-dimethylformamide at room temperature. After 2 h the reaction was quenched with 20 ml water. The mixture was extracted with 3 50-ml portions of ethyl acetate. The combined organic extracts were dried with sodium sulfate and concentrated. After drying in high vacuo at 50° C. and flash column chromatography 800 mg (70.4%) of the title compound was obtained as a white solid. As a side product 130 mg (11.4%) 4-chloro-6-phenoxy-nicotinic acid ethyl ester were also isolated.

후처리

  1. customAfter 2 h the reaction was quenched with 20 ml water
  2. extractionThe mixture was extracted with 3 50-ml portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. concentrationconcentrated
  5. customAfter drying in high vacuo at 50° C.

출처 및 근거

ORD 기록
ord-edb4110b83f84401924b374847de8d54
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596773B2

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