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

HRID 1294155노트

반응식

HRID 1294155 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4658ae750ce146b4ac34436421351ff9
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238716B2

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