Water → Agn-PC-0MW2M5

HRID 993428노트

반응식

HRID 993428 반응식
[C:1]1([CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S([CH2:28][N+:29]#[C-:30])(C1C=CC(C)=CC=1)(=O)=O.CC(C)([O-])C.[K+].O>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:16]([O:15][C:13]([C:12]1[C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[CH:30][NH:29][CH:28]=1)=[O:14])[CH3:17]

참가 물질

7

반응물 4

HCID 962WaterHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 53428571Ethyl 3-(naphthalen-1-yl)prop-2-enoate

생성물 1

HCID 9943237Agn-PC-0MW2M5수율 77%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21226206Ethyl acetate hexane용매

실험 절차

500 mg (1.89 mmol) of ethyl 3-(naphthalen-1-yl)acrylate prepared in EXAMPLE 80-1) and 368 mg (1.89 mmol) of tosylmethylisocyanide were dissolved in 10 ml of tetrahydrofuran. 255 mg (2.27 mmol) of potassium t-butoxide dissolved in tetrahydrofuran (10 ml) was slowly added thereto and the mixture was refluxed for 30 minutes. 10 ml of water was added to the reaction solution to stop the reaction and the solvent was removed under reduced pressure. The residue was extracted with diethylether, washed with aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to column chromatography(eluent: ethyl acetate/hexane=1/3, v/v) to give 385 mg (1.45 mmol, Yield 77%) of the title compound.

후처리

  1. additionwas slowly added
  2. temperaturethe mixture was refluxed for 30 minutes
  3. customthe reaction
  4. customthe solvent was removed under reduced pressure
  5. extractionThe residue was extracted with diethylether
  6. washwashed with aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-a8901ec5a8a54ee2a5a1f37bd5550948
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472526B1

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