2-Chloropyridine → Pyriproxyfen

HRID 1073518

반응식

HRID 1073518 반응식
[CH3:1][CH:2]([OH:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][CH:2]([O:18][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1

참가 물질

6

반응물 3

HCID 79772-ChloropyridineHCID 14798Sodium HydroxideHCID 103995681-(4-Phenoxyphenoxy)propan-2-ol

생성물 1

HCID 91753Pyriproxyfen수율 71%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

실험 절차

A mixture of 1-methyl-2-(4-phenoxyphenoxy)ethanol (2.0 g, 8.2 mmol), 2-chloropyridine (4.0 g, 35 mmol), flaked 95% sodium hydroxide (1 g, 24 mmol) and tetra-n-butylammonium bromide (0.13 g) was stirred at an inner temperature of 85° to 90° C. for 6 hours. After allowed to cool, toluene (10 g) was added thereto, and the resultant mixture was washed with water and extracted with 35% hydrochloric acid (5 g) twice. The hydrochloric acid layer was washed with toluene (10 g). A 10% aqueous sodium hydroxide solution was added thereto to make the mixture sufficiently basic. The basic mixture was further extracted with toluene (10 g) twice, and the toluene layer was washed with a 10% aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution in order and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give 2-[1-methyl- 2-(4-phenoxyphenoxy)ethoxy]pyridine (1.87 g) as white crystals.

후처리

  1. temperatureto cool
  2. washthe resultant mixture was washed with water
  3. extractionextracted with 35% hydrochloric acid (5 g) twice
  4. washThe hydrochloric acid layer was washed with toluene (10 g)
  5. additionA 10% aqueous sodium hydroxide solution was added
  6. extractionThe basic mixture was further extracted with toluene (10 g) twice
  7. washthe toluene layer was washed with a 10% aqueous sodium hydroxide solution
  8. dry with materiala saturated aqueous sodium chloride solution in order and dried over anhydrous magnesium sulfate
  9. customAfter removal of the solvent
  10. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9478d0c3a3944225adf0b02b98f51785
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04970222

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