HCID 19936860, compound → 1-[2-(1-Adamantyl)ethyl]-2-n-butyl-imidazol-5-carboxaldehyde

HRID 36990Notes

Reaction equation

HRID 36990 reaction equation
[C:1]12([CH2:11][CH2:12][N:13]3[C:17]([CH2:18][OH:19])=[CH:16][N:15]=[C:14]3[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:1]12([CH2:11][CH2:12][N:13]3[C:17]([CH:18]=[O:19])=[CH:16][N:15]=[C:14]3[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 1

HCID 19936860HCID 19936860, compound

Product 1

HCID 199369031-[2-(1-Adamantyl)ethyl]-2-n-butyl-imidazol-5-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

The above prepared compound (5.4 g) was stirred at room temperature with potassium hydroxide (5.2 g) in ethanol (200 ml) for one hour. The mixture was concentrated, poured into water, stirred and filtered to give 1-[2-(1-adamantyl)ethyl]-2-n-butyl-5-hydroxymethyl-imidazole. The hydroxymethyl group was oxidized by refluxing the imidazole compound (51.1 g) with manganese dioxide (20.3 g) in toluene (200 ml) to give 1-[2-(1-adamantyl)ethyl]-2-n-butyl-imidazol-5-carboxaldehyde.

Sources & evidence

ORD record
ord-5ca69039501649b5a557b667f98d3fb6
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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