Dimethyl Sulfoxide → 2-Methyl-5-(oxiran-2-yl)pyridine

HRID 1045533노트

반응식

HRID 1045533 반응식
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][N:14]=1>C1COCC1>[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]2[CH2:8][O:18]2)=[CH:15][N:14]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 101925666-Methyl-3-pyridinecarboxaldehyde

생성물 1

HCID 157135882-Methyl-5-(oxiran-2-yl)pyridine수율 137.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

The title compound was prepared by following general procedure 3. DMSO (4mL) was added to NaH 60% dispersion in oil (0.314 g, 7.8 mmol, 1.3 equiv.) and heated to 65° C. for 1 h. THF (10mL) was added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture was cooled to 0° C. Trimethylsulfonium iodide (1.2 g, 5.9 mmol, 1 equiv.) was added and stirred for 10 min. and then a solution of 6-methylnicotinaldehyde (0.720 g, 5.9 mmol, 1 equiv.) in THF was added dropwise. After complete addition, the reaction mixture was stirred at RT for 2 h, the product was detected by LCMS. The reaction mixture was poured into ice water and the product was extracted in diethyl ether (4×50 mL), dried over Na2SO4 and concentrated at 25° C. to get the crude product 2-methyl-5-(oxiran-2-yl)pyridine (1.1 g crude).

후처리

  1. customThe title compound was prepared
  2. temperatureheated for another 10 min
  3. temperaturethe reaction mixture was cooled to 0° C
  4. additionAfter complete addition
  5. stirringthe reaction mixture was stirred at RT for 2 h
  6. extractionthe product was extracted in diethyl ether (4×50 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated at 25° C.

출처 및 근거

ORD 기록
ord-a6b9b5110b0744edaba990fa820ea733
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569287B2

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