Dimethylformamide → 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine

HRID 33512노트

반응식

HRID 33512 반응식
S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:13]=[C:14]([C:18]2[N:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1>ClCCl>[Cl:3][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:27])([F:26])[F:10])[CH:13]=2)=[N:23][CH:22]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24729887(6-(3-(Trifluoromethyl)phenyl)pyridin-3-YL)methanol

생성물 1

HCID 691065005-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine수율 72.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

911 mg (0.56 ml, 7.66 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 970 mg (3.83 mmol) [6-(3-Trifluoromethyl-phenyl)-pyridine-3-yl]-methanol in 30 ml dichloromethane, stirred for 5 min. at 0° C., and at r.t. for 1 h. The mixture is poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), and evaporated. Purification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 750 mg (72%) of 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine as light yellow crystals

후처리

  1. waitat r.t. for 1 h
  2. additionThe mixture is poured on ice/sodium bicarbonate solution
  3. customthe organic phase separated
  4. extractionThe water phase is extracted with dichloromethane
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (sodium sulphate)
  7. customevaporated
  8. customPurification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3)

출처 및 근거

ORD 기록
ord-d6c9e3c17fa240de9127e0949efdfbda
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429605B2

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