2-Chloropyridine → Pyriproxyfen

HRID 1073513

반응식

HRID 1073513 반응식
[H-].[Na+].[CH3:3][CH:4]([OH:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.[H][H].Cl[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>CN(C)C=O.O>[CH3:3][CH:4]([O:20][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 79772-ChloropyridineHCID 24758Sodium hydrideHCID 103995681-(4-Phenoxyphenoxy)propan-2-olHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 91753Pyriproxyfen수율 79%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of sodium hydride (200 mg, 5.0 mmol; 60% in oil) in dimethylformamide (5 ml), a solution of 1-methyl-2-(4-phenoxyphenoxy)ethanol (1.22 g, 5.0 mmol) in dimethylformamide (3 ml) was dropwise added with stirring, and the mixture was kept at an inner temperature of 50° to 60° C. until the generation of hydrogen gas ceased. 2-Chloropyridine (684 mg, 6.0 mmol) was dropwise added thereto, followed by stirring at 100° to 110° C. for 5 hours. The reaction mixture was cooled to room temperature, poured into water (100 ml) and extracted with toluene (40 ml) three times. The toluene layer was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography to give 2-[1-methyl-2-(4-phenoxyphenoxy)ethoxy] pyridine (1.27 g) as pale yellow liquid. nD20.5 1.5823. Upon being allowed to stand for a few days, the liquid solidified to give crystals. M.P., 49.7° C.

후처리

  1. stirringby stirring at 100° to 110° C. for 5 hours
  2. extractionextracted with toluene (40 ml) three times
  3. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-38987a05ccc84a4cbc15b28bb1829721
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04970222

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