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

HRID 2081857Notes

Reaction equation

HRID 2081857 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-5e45d1dd91754fffa7d73db5a53eddf1
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Reaction notes

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