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

HRID 1294155ノート

反応式

HRID 1294155 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:19]=[C:18]([CH2:20]O)[O:17][N:16]=1.S(Cl)([Cl:24])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:24][CH2:20][C:18]1[O: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:19]=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

To a solution of 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol (2.86 g) in toluene (50 ml) was slowly added thionyl chloride (0.80 mL) at room temperature and the mixture was stirred under reflux for 30 min. After cooling, the reaction mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 5-chloromethyl-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)isoxazole (2.70 g, yield 89%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 105-106° C.

後処理

  1. customat room temperature
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-4658ae750ce146b4ac34436421351ff9
出典データセット
uspto-grants-2007_07
特許番号
US07238716B2

反応ノート

読み込み中…