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

HRID 1387320
Notes
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Reaction equation

HRID 1387320 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 161915Tosylmethyl isocyanideHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d4378d26cee04034b40423a173bf5b66
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06268363B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes