Thionyl Chloride → 5-(Chloromethyl)-2-phenylpyridine

HRID 914457노트

반응식

HRID 914457 반응식
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:17])=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:17][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][CH:11]=1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 22254216(6-Phenylpyridin-3-yl)methanol

생성물 1

HCID 27638625-(Chloromethyl)-2-phenylpyridine수율 81.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(6-Phenylpyridin-3-yl)methanol (15.0 g) synthesized in Reference Example 20 was dissolved in dichloromethane (150 mL) and, after ice-cooling, thionyl chloride (12.5 g) was added to, and the mixture was stirred at 0° C. for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1) to give the title compound (13.5 g) as a white solid.

후처리

  1. temperatureafter ice-cooling
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-2627eded853a4259841bcc350375e081
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026370B2

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