Pyridine N-Oxide → Benzopyran

HRID 1449779

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HRID 1449779 반응식
[N+]1([O-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([C:10]1C=C[CH:13]=[CH:12][CH:11]=1)=O.CCCCCC.C([OH:25])(C)C>C(#N)C>[O:25]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:6][C:5]=2[CH:4]=[CH:3][CH2:2]1

참가 물질

5

반응물 3

HCID 12753Pyridine N-OxideHCID 92125IodosylbenzeneHCID 21585144Isopropanol hexane

생성물 1

HCID 9211Benzopyran수율 98%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

26.2 mg of compound [IV-1] (0.10 mmol) and 2.6 mg of the compound [Ia -1] (2.5 μmol) were dissolved in 1.25 mL of an acetonitrile solution of pyridine-N-oxide (0.02 M, 0.025 mmol), followed by cooling to 0° C. To the resulting solution was added 44.0 mg of iodosylbenzene (0.20 mmol) all at once under a nitrogen atmosphere, followed by stirring at 0° C. for twenty four hours. Insoluble matters were filtered out through Celite, the filtrate was concentrated, and the residues were purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:2-4:6) to obtain the intended compound. (epoxide yield: 20.1 mg (72%)) (asymmetric yield: 98% e.e.) (Daicel Chiralcel OJ, hexane-isopropanol=1:1, flow rate: 0.5 mL/min.)

후처리

  1. filtrationInsoluble matters were filtered out through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe residues were purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:2-4:6)
  4. customto obtain the intended compound

출처 및 근거

ORD 기록
ord-fa17b706d8ac49ca89e941d4ffe17a33
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599957

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