Sodium Thiosulfate → Methyl 6-phenylpyridine-2-carboxylate 1-oxide

HRID 2095779노트

반응식

HRID 2095779 반응식
[C:1]1([C:7]2[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N+:12]=2[O-:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11127604Methyl 6-phenylpyridine-2-carboxylate

생성물 1

HCID 66968602Methyl 6-phenylpyridine-2-carboxylate 1-oxide수율 10%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 6-phenylpyridine-2-carboxylate (509 mg, 6.24 mmol) in dichloromethane (5 mL) was added m-chloroperbenzoic acid (purity: 69-75%, 2.87 g, 12.5 mmol), and the mixture was stirred at room temperature for 3 days. Saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1) to give the title compound (142 mg, 10%) as a colorless oil.

후처리

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1)

출처 및 근거

ORD 기록
ord-73b9332c468240609e0f805f3f167ae1
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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