Dimethylformamide → methyl 3-[1-(phenoxyacetyl)-2,3-dihydro-1H-pyrrol-3-yl]benzoate

HRID 504399

Reaktionsgleichung

Reaktionsgleichung von HRID 504399
N1(C(OC[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)CC=CC1.Br[C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21].[C:27]([O-:30])(=O)C.[K+].[CH3:32][N:33]([CH3:36])[CH:34]=[O:35].[CH3:37][CH2:38]OC(C)=O>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[O:30]([CH2:27][C:34]([N:33]1[CH:36]=[CH:38][CH:37]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH2:32]1)=[O:35])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

9

Edukt 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 12070Methyl 3-bromobenzoateHCID 517044Potassium AcetateHCID 643471Benzyl 3-pyrroline-1-carboxylate

Produkt 1

HCID 66662462methyl 3-[1-(phenoxyacetyl)-2,3-dihydro-1H-pyrrol-3-yl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (0.626 mL, 0.00349 mol), methyl 3-bromo-benzoate (300 mg, 0.001 mol), palladium(II) diacetate (14 mg, 0.000063 mol), potassium acetate (356 mg, 0.00363 mol), and tetra-N-butylammonium bromide (4.50×10−2 mg, 0.00140 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was stirred under nitrogen at 40° C. for 4 days. The reaction mixture was diluted with AcOEt and water. The organic layer was separated and the aqueous layer was extracted with AcOEt. The combined organic layer was washed with brine, dried with MgSO4, and concentrated to afford the crude product. The crude product was purified by flash chromatography, eluting with 30% AcOEt in hexanes.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with AcOEt
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-508907cfc2de43d58ce1741d2c556de4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776874B2

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