Ethyl 2-(diphenylmethyleneamino)acetate → ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

HRID 454446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454446
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Cs+].Br[CH2:25][CH:26]=[C:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:1]1([C:7](=[N:8][CH:9]([CH2:25][CH:26]=[C:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 219961434-(2-Bromoethylidene)tetrahydro-2H-pyranHCID 23679066Caesium hydroxide--water (1/1/1)

Produkt 1

HCID 58313138ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl N-(diphenylmethylidene)glycinate (5.29 g, 19.8 mmol), benzyltriethylammonium chloride (0.41 g, 1.8 mmol) and cesium hydroxide monohydrate (4.54 g, 27.0 mmol) in anhydrous dichloromethane (50 mL) was added 4-(2-bromoethylidene)tetrahydro-2H-pyran (3.44 g, 18.0 mmol) as a solution in anhydrous dichloromethane (40 mL) and the reaction stirred at room temperature for 72 h under nitrogen. The reaction was partitioned between dichloromethane and water and the aqueous layer was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 5-40% hexanes/EtOAc to afford the title compound as a clear oil in quantitative yield.

Aufarbeitung

  1. customThe reaction was partitioned between dichloromethane and water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 5-40% hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-6dfa388c81714002bc7f914b724ce22e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492554B2

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