Thionyl Chloride → 5-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolyl)methoxypyridine

HRID 349982

반응식

HRID 349982 반응식
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:3][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:6]=2[CH3:5])=[N:24][CH:23]=1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178328032-(5-Methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-methanol

생성물 1

HCID 178328085-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolyl)methoxypyridine수율 90.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Thionyl chloride (5.39 g) was added to a mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol (12.2 g) and toluene (200 ml), which was stirred at room temperature for 1 hour. Ice water was added to the reaction mixture, which was neutralized with saturated aqueous sodium bicarbonate solution, and was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 5-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (11.7 g, yield 90%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane to obtain colorless prism crystals. Melting point: 86–87° C.

후처리

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9af92987d832474197664dbd89c76871
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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