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Water → Naphthalen-1-yl(1H-pyrrol-3-yl)methanone

HRID 1387320
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HRID 1387320 반응식
S([CH2:11][N+:12]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[CH3:14][C:15](C)([O-:17])[CH3:16].[K+].O.C(O[CH2:25][CH3:26])(=O)C.[CH3:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O1C[CH2:36][CH2:35][CH2:34]1>>[C:14]1([C:15]([C:16]2[CH:26]=[CH:25][NH:12][CH:11]=2)=[O:17])[C:36]2[C:30](=[CH:31][CH:32]=[CH:34][CH:35]=2)[CH:29]=[CH:28][CH:27]=1
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참가 물질

6

반응물 5

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 161915Tosylmethyl isocyanideHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 15832251Naphthalen-1-yl(1H-pyrrol-3-yl)methanone수율 80%

실험 절차

901 mg(5 mmol) of the compound prepared in Preparation 49-2) and 1.01 g(5.5 mmol) of tosylmethylisocyanide were dissolved in 10 ml of tetrahydrofuran. 555 mg(5.5 mmol) of potassium t-butoxide dissolved in 10 ml of tetrahydrofuran was slowly added thereto and the mixture was stirred 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. 20 ml of water was added to the residue and the resulting mixture was extracted with ethyl acetate, washed with aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to silica gel column chromatography(eluent: ethyl acetate/hexane=1/3, v/v) to obtain 884 mg(4 mmol, Yield 80%) of the title compound.

후처리

  1. additionwas slowly added
  2. customthe reaction
  3. customthe solvent was removed under reduced pressure
  4. addition20 ml of water was added to the residue
  5. extractionthe resulting mixture was extracted with ethyl acetate
  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-d4378d26cee04034b40423a173bf5b66
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06268363B1

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