Ethyl formate → HCID 178517727, Verbindung

HRID 657164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657164
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]([O:13]CC)=O.[CH:16](OCC)=O.[C:21]1(/[CH:27]=[CH:28]/[C:29](=[NH:31])[NH2:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.CO.CCO.C1COCC1>[C:21]1(/[CH:27]=[CH:28]/[C:29]2[NH:31][CH:16]=[C:10]([O:9][CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8][O:3]3)[C:11](=[O:13])[N:30]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

8

Edukt 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 10899396ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetateHCID 14668188Cinnamimidamide

Produkt 1

HCID 178517727HCID 178517727, VerbindungAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 18681192Ethanol, mixt. with methanolLösungsmittel

Versuchsvorschrift

NaH (0.38 g, 9.5 mmol, 60% paraffin oil) was added slowly to a THF (20 mL) solution of ethyl (tetrahydro-2H-pyran-2-yloxy)acetate (prepared by treating ethyl hydroxyacetate with 3,4-dihydro-2H-pyran and TsOH) (1.0 g, 5.3 mmol) and dry ethyl formate (3.9 g, 53 mmol). The reaction mixture was stirred at room temperature for 15 min. and then heated at 65° C. for 45 min. The reaction mixture was concentrated to dryness to give a pale yellow solid. The solid was added to a MeOH/EtOH (20 mL/20 mL) solution of (2E)-3-phenyl-2-propenimidamide (0.78 g, 5.3 mmol), the subsequent mixture was heated at 80° C. for 4 h. The resulting material was poured into DCM (10 mL) containing silica gel (3 g) and evaporated. Purification by column chromatography (silica gel) using a MeOH/DCM gradient (0-10%) provided the desired product as a pale yellow solid (1 g, 63%).

Aufarbeitung

  1. temperatureheated at 65° C. for 45 min
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customto give a pale yellow solid
  4. temperaturethe subsequent mixture was heated at 80° C. for 4 h
  5. additioncontaining silica gel (3 g)
  6. customevaporated
  7. customPurification by column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-6879b79ccf234b85af1804df33b3675c
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

Notizen zur Reaktion

Wird geladen…