Reaction #65291

Reaction equation

potassium acetate

2-n-butyl-1-(4-carbomethoxy-3-methoxymethoxyphenyl)methyl-4-chloro-1H-imidazol-5-carboxaldehyde

→

product

Yield 87.0%

2-n-butyl-1-(4-carbomethoxy-3-methoxymethoxyphenyl)methyl-1-H-imidazol-5-carboxaldehyde

Yield 87.0%

Solvents

methanol

methanol

Conditions

Workup

1. 1
   FiltrationThe solid was filtered
2. 2
   Concentrationthe filtrate was concentrated in vacuo
3. 3
   OtherThe residue was partitioned between diethyl ether and water
4. 4
   OtherThe layers were separated
5. 5
   Washthe organic layer was washed with brine
6. 6
   Dryingdried with magnesium sulfate
7. 7
   OtherThe solvent was removed in vacuo

Procedure

To a suspension of 0.32 g of 10% palladium on carbon in 15 mL of methanol containing potassium acetate (0.813 g, 8.28 mmol) was added a solution of 2-n-butyl-1-(4-carbomethoxy-3-methoxymethoxyphenyl)methyl-4-chloro-1H-imidazol-5-carboxaldehyde (3.27 g, 8.28 mmol) in 60 mL of methanol. The reaction was hydrogenated at 4 psi for 40 minutes. The solid was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between diethyl ether and water. The pH of the aqueous layer was adjusted to 7.5 with 5% sodium carbonate solution. The layers were separated and the organic layer was washed with brine and dried with magnesium sulfate. The solvent was removed in vacuo to give 2.59 g (87%) of product as an oil.

Source