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

HRID 271469

反応式

HRID 271469 の反応式
[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

参加物

6

反応物 3

HCID 5943Carbon TetrachlorideHCID 31398Chlorosuccinimide2 回HCID 598348122-Methyl-5-(1,2-oxazol-3-yl)pyridine

生成物 1

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

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-45b2a6bef758469b9fa314c84e355dcd
出典データセット
uspto-grants-2008_11
特許番号
US07452892B2

関連ノート

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