Water → (Naphthalen-1-yl)(1H-pyrrol-3-yl)methanone
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]=1Participants
Procedure
901 mg(5 mmol) of the compound prepared in Preparation 5-2) and 1.01 g(5.5 mmol) of tosylmethylisocyanide were dissolved in 10 ml of tetrahydrofuran, and then 555 mg(5.5 mmol) of potassium t-butoxide in tetrahydrofuran(10 ml) was slowly added thereto. The reaction solution was stirred for 30 minutes and 10 ml of water was added to the solution in order to stop the reaction. The solvent was removed under reduced pressure. 20 ml of water was added to the residue, which was then 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 column chromatography(eluent: ethyl acetate/n-hexane=1/3, v/v) to obtain 884 mg(4 mmol, Yield 80%) of the title compound.
Workup
- customthe reaction
- customThe solvent was removed under reduced pressure
- addition20 ml of water was added to the residue, which
- extractionwas then extracted with ethyl acetate
- washwashed with aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-b2cc3cd5f0f148ef906e3862401e6b82
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06436960B1
Reaction notes
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