3-(4-Bromophenyl)cyclobutan-1-one → HCID 178521618, Verbindung

HRID 1988134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988134
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][C:10](=[O:12])[CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:9][C@H:10]([OH:12])[CH2:11]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 45896953-(4-Bromophenyl)cyclobutan-1-oneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 178521618HCID 178521618, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 3-(4-bromo-phenyl)-cyclobutanone (3 g, 13.3 mmol) (J. Med. Chem., 43:721-735(2000)), in anhydrous ether (100 mL) cooled to −20° C. was dropwise added lithium aluminum hydride (1M in THF, 15 mL). The mixture was then allowed to warm to room temperature and stirred for 4 hours. The reaction was slowly quenched with NaOH (1M, 0.8 mL), H2O (0.8 mL) and NaOH (1M, 0.8 mL) sequentially. After stirring for about 30 minutes, the mixture was filtered through a layer of diatomaceous earth and washed with extra ether (100 mL). The filtrate was evaporated under reduced pressure to provide a colorless oil as the title compound (3.01 g, 100%). 1H NMR (300 MHz, CDCl3) δ 2.0 (m, 2 H), 2.76 (m, 2 H), 2.92 (m, 1 H), 4.28 (m, 1 H), 7.09 (d, J=9 Hz, 2 H), 7.41 (d, J=9 Hz, 2 H); (DCl/NH3) m/z 244 (M+NH4)+.

Aufarbeitung

  1. customThe reaction was slowly quenched with NaOH (1M, 0.8 mL), H2O (0.8 mL) and NaOH (1M, 0.8 mL) sequentially
  2. stirringAfter stirring for about 30 minutes
  3. filtrationthe mixture was filtered through a layer of diatomaceous earth
  4. washwashed with extra ether (100 mL)
  5. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3544738fa9334258a8a6263fe809a821
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553964B2

Notizen zur Reaktion

Wird geladen…