Thionyl Chloride → 4-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine

HRID 349949ノート

反応式

HRID 349949 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH2:21]O)[CH:18]=[CH:17][N:16]=1.S(Cl)([Cl:25])=O>>[Cl:25][CH2:21][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])[CH:20]=1

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 178613752-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanol

生成物 1

HCID 178613044-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine収率 54%

実験手順

A mixture of 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanol (1.19 g) and thionyl chloride (4 ml) was stirred at room temperature for 1 hour. After the reaction mixture was concentrated, saturated aqueous sodium bicarbonate solution was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 4-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (680 mg, yield 54%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 104–105° C.

後処理

  1. concentrationAfter the reaction mixture was concentrated
  2. additionsaturated aqueous sodium bicarbonate solution was added to the mixture, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-25059e32088b40fdb830d3eb898ddc18
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

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