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

HRID 1514695
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인쇄 미리보기

반응식

HRID 1514695 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]([Cl: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]([Cl:31])=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:34])=[N:6][CH:5]=1
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참가 물질

7

반응물 2

HCID 23667635Sodium periodateHCID 667181406-[3-(4-Chloro-phenyl)-5-([E]-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

생성물 1

HCID 866462556-[3-(4-Chloro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester수율 65%

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 66133
Benzyl triethylammonium chloride
촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

6-[3-(4-Chloro-phenyl)-5-([E]-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (6.35 g, 14.2 mmol) was treated with osmium(VIII) oxide (90.3 mg, 355 μmol), sodium metaperiodate (12.2 g, 56.8 mmol) and benzyltriethylammonium chloride (1.32 mg, 5.68 mmol) in dioxane (140 mL) and water (47 mL). The mixture was heated for 35 min at 120° C. in a microwave. Extraction with ethyl acetate/water and chromatogaphy (silica, ethyl acetate:heptane 1:9 to 1:1) afforded the title compound (3.43 g, 65%) as a white solid. MS: m/e=373.1 [M+H]+.

후처리

  1. extractionExtraction with ethyl acetate/water and chromatogaphy (silica, ethyl acetate:heptane 1:9 to 1:1)

출처 및 근거

ORD 기록
ord-5f192a90ada34554a400f58e98c6c25c
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222246B2

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