Carbon Tetrachloride → 2-(Chloromethyl)-5-(1,2-oxazol-3-yl)pyridine

HRID 271469

반응식

HRID 271469 반응식
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)[Cl:14].ClN1C(=O)CCC1=O>CCOC(C)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:14][CH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 5943Carbon TetrachlorideHCID 31398Chlorosuccinimide2회HCID 598348122-Methyl-5-(1,2-oxazol-3-yl)pyridine

생성물 1

HCID 598348302-(Chloromethyl)-5-(1,2-oxazol-3-yl)pyridine수율 34%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 8857Ethyl Acetate용매

실험 절차

To a stirring mixture of 3-(6-methylpyridin-3-yl)isoxazole (76 mg, 0.474 mmol) and 6 mL carbon tetrachloride, was added N-chlorosuccinimide (69.7 mg, 0.52 mmol), followed by 3 mg benzoyl peroxide. The reaction mixture was refluxed. Additional N-chlorosuccinimide (40 mg, 0.30 mmol) was added in two portions after stirring 2 h and 4 h. After refluxing for a total of 13 h the reaction mixture was diluted with EtOAc, then washed sequentially with 1 N aq. NaOH solution, water and saturated aqueous NaCl. The organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 31 mg (34%) of the title compound as a white solid. HPLC/MS: retention time=1.77 min, [M+H]+=195.

후처리

  1. temperatureThe reaction mixture was refluxed
  2. temperatureAfter refluxing for a total of 13 h the reaction mixture
  3. washwashed sequentially with 1 N aq. NaOH solution, water and saturated aqueous NaCl
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-45b2a6bef758469b9fa314c84e355dcd
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

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