Ethyl 4-chlorobutyrate → HCID 19429294, compound

Temperature

70 °C

Ethyl 4-chlorobutyrate (7.0 g) was added at room temperature to a solution of 5-methyl-4-imidazole-carbaldehyde (4.17 g) and 60% oily sodium hydride (2.0 g) in 50 ml dimethylformamide (prepared by stirring at 50° C. for one hour). The resulting mixture was heated at 70° C. for four hours and then concentrated to dryness under reduced ressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer collected was washed with water and then with saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dried solution was concentrated to dryness under reduced pressure, and the residue was subjected to column chromatography on silica gel (80 g). Elution with ethyl acetate gave 2.35 g (28%) of an about 1:1 mixture of 1-(3-ethoxycarbonylpropyl)-5-methyl-4-imidazole-carbaldehyde and 1-(3-ethoxylcarbonylpropyl)-4-methyl-5-imidazole-carbaldehyde.

1. concentrationconcentrated to dryness under reduced ressure, water
2. additionwas added to the residue
3. extractionthe mixture was extracted with ethyl acetate
4. customThe organic layer collected
5. washwas washed with water
6. dry with materialwith saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
7. concentrationThe dried solution was concentrated to dryness under reduced pressure
8. washElution with ethyl acetate
9. customgave 2.35 g (28%) of an

ORD record

ord-cbaeda8785374beaacb29e361a9107cd

Source dataset

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05336679