Water → 4-Phenylbicyclo[2.2.2]octane-1-carboxaldehyde

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Reaktionsgleichung

CON(C)[C:4]([C:6]12[CH2:13][CH2:12][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.CCOC(C)=O>C1COCC1>[C:14]1([C:9]23[CH2:12][CH2:13][C:6]([CH:4]=[O:5])([CH2:11][CH2:10]2)[CH2:7][CH2:8]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To an ice water cooled solution of N-methoxy-N-methyl-1-phenylbicyclo[2.2.2]octane-4-carboxamide (Intermediate 5; 8.49 g, 31.05 mmol) in anhydrous THF (100 mL) under nitrogen was added lithium aluminium hydride (1M solution in THF, 62 mL) dropwise and the reaction mixture was allowed to stir at 0° C. for 1 hr. Water (25 mL) was added cautiously followed by EtOAc (˜100 mL) and the mixture was filtered through a pad of celite washing with EtOAc (50 mL). The filtrate was washed with brine (150 mL), the organic phase separated, dried (MgSO4) and concentrated to leave the title compound as a colourless oil which formed a solid on standing (6.92 g, 32.28 mmol, 100%); 1H NMR (CDCl3) δ 1.72-1.83 (6H, m), 1.87-1.94 (6H, m), 7.17-7.22 (1H, m), 7.31-7.33 (4H, m), 9.53 (1H, s); GC-MS EI m/e M+ 214.

Aufarbeitung

filtrationthe mixture was filtered through a pad of celite
washwashing with EtOAc (50 mL)
washThe filtrate was washed with brine (150 mL)
customthe organic phase separated
dry with materialdried (MgSO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-d7556b3d72374c619cfc6200c1c2fdf3
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08017603B2

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