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Water ethylacetate → 6-(5-Formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile

HRID 1514728
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인쇄 미리보기

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HRID 1514728 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([CH2:12][O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[C:10](/[CH:22]=C/C2C=CC=CC=2)[O:9][N:8]=1.I([O-])(=O)(=O)=[O:31].[Na+].C(OCC)(=O)C.O>C(O)(C)(C)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH:22]([C:10]1[O:9][N:8]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:11]=1[CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1)=[O:31]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 3

HCID 22728543Water ethylacetateHCID 23667635Sodium periodateHCID 667182056-[3-Pyridin-2-yl-5-([E]-styryl)-isoxazol-4-ylmethoxy]-nicotinonitrile

생성물 1

HCID 866462576-(5-Formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile수율 51%

시약·촉매·용매 5

HCID 30318Osmium Tetroxide촉매
HCID 66133
Benzyl triethylammonium chloride
촉매
HCID 962Water용매
HCID 6386tert-Butanol용매
HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A mixture of 6-[3-pyridin-2-yl-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinonitrile (0.57 g, 2 mmol), osmium(VIII) oxide solution (0.38 mL of a 2.5% solution in tert-butanol, 0.04 mmol), sodium metaperiodate (1.29 g, 6 mmol), benzyltriethylammonium chloride (0.14 g, 0.6 mmol) in dioxane (13 mL) and water (4.5 mL) was heated in a microwave for 45 min at 120° C. Extractive workup (ethyl acetate/water) was followed by drying of the organic phase over sodium sulfate and filtering. The solvent was evaporated and the residue was triturated with diisopropylether to afford the title compound (0.23 g, 51%) as a white solid. MS: m/e=307.2 [M+H]+.

후처리

  1. dry with materialby drying of the organic phase over sodium sulfate
  2. filtrationfiltering
  3. customThe solvent was evaporated
  4. customthe residue was triturated with diisopropylether

출처 및 근거

ORD 기록
ord-d48c01973882400b9972a5ba40cc42b9
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222246B2

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