Potassium Carbonate → (3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

HRID 965205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965205
Cl[C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[NH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[CH2:15]([O:14][C:12]1[O:13][C@H:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][C@H:3]2[N:11]=1)[CH3:16]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 7070371trans-1-Chloro-2-ethoxycarbonylaminoindane

Produkt 1

HCID 18661302(3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of (±) trans-1-chloro-2-ethoxycarbonylaminoindane (B. J. Walker and P. J. Wrobel, J. Chem. Soc. Chem. Commun., 1980, 462)(4.0 g, 0.017 mol) in ethanol (125 ml) was treated with K2CO3 (2.4 g, 0.018 mol) and diluted with water (50 ml). After stirring at room temperature for 20 h, the reaction was concentrated under high vacuum to approximately one quarter the original volume, then diluted with water (25 ml) and extracted into diethyl ether (3×50 ml). The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo to give the title compound as a low melting solid (3.3 g), m.p 53°-54° C. (from diethyl ether/n-pentane).

Aufarbeitung

  1. concentrationthe reaction was concentrated under high vacuum to approximately one quarter the original volume
  2. additiondiluted with water (25 ml)
  3. extractionextracted into diethyl ether (3×50 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-99d327fa069d422fadc2dd1db8ddd58a
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773463

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