HCID 69212492, compound → HCID 85937142, compound

HRID 2252048Notes

Reaction equation

HRID 2252048 reaction equation
[C:1]([O:5][C:6]([N:8]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)[CH2:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(#N)C.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([N:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH2:9][CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 69212492HCID 69212492, compound

Product 1

HCID 85937142HCID 85937142, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Dissolve 4-(N-tert-butoxycarbonyl-N-ethyl-amino)-benzyl alcohol (1.24 g, 5.52 mmol) in 50 mL acetonitrile. Add to this solution manganese dioxide and stir the mixture for two days at room temperature. Filter the residue through Celite® and concentrate the solvent to give 632 mg of 4-(N-tert-butoxycarbonyl-N-ethyl-amino) benzaldehyde. Yield 52%. 1H-NMR (CDCl3, 300 MHz): 9.95 (s, 1H); 7.83 (d, J=8.7 Hz, 2H); 7.39 (d, J=8.7 Hz, 2H); 3.74 (q, J=7.0 Hz, 2H); 1.45 (s, 9H); 1.18 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationFilter the residue through Celite®
  2. concentrationconcentrate the solvent

Sources & evidence

ORD record
ord-ab1ad4fb6bab470182ec80f4340d0257
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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