Ethyl Acetate → HCID 22168453, Verbindung

HRID 390371

Reaktionsgleichung

Reaktionsgleichung von HRID 390371
C[C:2]1(C)[N:7]([O])[C:6](C)(C)[CH2:5][CH:4](O)[CH2:3]1.C1(C(O)=O)CC1.[CH2:19]1[CH2:24][CH2:23][CH:22]([N:25]=[C:26]=[N:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:21][CH2:20]1.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.ClCCl.CCCCCC>[CH2:31]1[CH2:30][CH2:29][CH:28]([N:27]=[C:26]=[N:25][CH:22]2[CH2:23][CH2:24][CH2:19][CH2:20][CH2:21]2)[CH2:33][CH2:32]1.[CH3:22][N:25]([C:4]1[CH:3]=[CH:2][N:7]=[CH:6][CH:5]=1)[CH3:26]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 15655Cyclopropanecarboxylic acidHCID 137994Tempol

Produkt 1

HCID 22168453HCID 22168453, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of Tempol (1.72 g, 0.01 mmole), cyclopropanecarboxylic acid (0.946 g, 0.011 mmole), and DMAP (0.12, 0.001 mmole) in dichloromethane (25 ml) was added DCC (2.27 g, 0.11 mmole) and the mixture was stirred overnight at room temperature. The mixture was filtered over celite and the solution was evaporated under reduced pressure. The product was isolated by silica gel column chromatography using first hexane and then 10% ethyl acetate in hexane. Yield: 2.26 g (94.1). IR and NMR were consistent with the assigned structure.

Aufarbeitung

  1. filtrationThe mixture was filtered over celite
  2. customthe solution was evaporated under reduced pressure
  3. customThe product was isolated by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-63ec673a24ab40a1adfad9ee2f981012
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383648B2

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