Thionyl Chloride → 5-Chloromethyl-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)isoxazole

HRID 349959ノート

反応式

HRID 349959 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[CH:23]=[C:22]([CH2:24]O)[O:21][N:20]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:3][CH2:24][C:22]1[O:21][N: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])[CH:23]=1

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178612053-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol

生成物 1

HCID 178612855-Chloromethyl-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)isoxazole収率 89%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Thionyl chloride (0.80 ml) was added slowly to a solution of 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol (2.86 g) in toluene (50 ml) at room temperature, which was stirred for 30 minutes under reflux. After cooling, the reaction mixture was poured into saturated aqueous sodium bicarbonate solution, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated to obtain 5-chloromethyl-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)isoxazole (2.70 g, yield 89%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 105–106° C.

後処理

  1. temperatureunder reflux
  2. temperatureAfter cooling
  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-c9101ebabe154b54af7aee6011d3abad
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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