Sodium periodate → 6-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

HRID 1514677노트

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HRID 1514677 반응식
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2/[CH:17]=C/C2C=CC=CC=2)=[N:6][CH:5]=1.I([O-])(=O)(=O)=[O:34].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:34])=[N:6][CH:5]=1

참가 물질

7

반응물 2

HCID 23667635Sodium periodateHCID 667182126-[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

생성물 1

HCID 866462546-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester수율 78.2%

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A mixture of 6-[3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (3.88 g, 9.01 mmol), osmium(VIII) oxide (57.3 mg, 0.23 mmol), sodium metaperiodate (7.71 g, 36.1 mmol), benzyltriethylammonium chloride (838 mg, 3.61 mmol) in dioxane (60 mL) and water (20 mL) was heated for 15 min at 120° C. in a microwave. Water was then added to the reaction mixture and the resulting mixture extracted with ethyl acetate. The organic extract was then evaporated and the residue purified by chromatography (silica, ethyl acetate:heptane=1:4 to 2:3) to afford the title compound (2.51 g, 78%) as off white oil. MS: m/e=357.2 [M+H]+.

후처리

  1. extractionthe resulting mixture extracted with ethyl acetate
  2. extractionThe organic extract
  3. customwas then evaporated
  4. customthe residue purified by chromatography (silica, ethyl acetate:heptane=1:4 to 2:3)

출처 및 근거

ORD 기록
ord-ed091781e5a841d8967db3e5f1fe3a8d
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222246B2

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