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

HRID 908111Notes

Reaction equation

HRID 908111 reaction equation
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

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 59379799N-methoxy-N-methyl-1-phenylbicyclo[2.2.2]octane-4-carboxamide2×

Product 1

HCID 593797914-Phenylbicyclo[2.2.2]octane-1-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d7556b3d72374c619cfc6200c1c2fdf3
Source dataset
uspto-grants-2011_09
Patent number
US08017603B2

Reaction notes

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