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

HRID 349982

反応式

HRID 349982 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9af92987d832474197664dbd89c76871
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

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