4-oxopentanoic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of dicyclohexylcarbodiimide (0.084 g, 0.216 mmol) in dichloromethane (1 ml) was added to a solution of levulinic acid (0.047 g, 0.406 mmol) in dichloromethane (2 ml). A white crystalline solid of dicyclohexylurea formed immediately. The suspension was allowed to stand at room temperature for 30 min, then chilled in an ice bath for 3 h min, and left to stand at 4° overnight before filtration. The colourless filtrate was concentrated to give a colourless oil with a small amount of suspended white solid of dicyclohexylcarbodiimide (DCC) and dicyclohexylurea (DCU). This was used as crude in the preparation of (3).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A! Starting from 10 g (0.086 mole) of levulinic acid, 11.8 ml (0.086 mole) of triethylamine, 11.2 ml (0.086 mole) of isobutyl chloroformate and 13.3 ml (0.103 mole) of N-methyl-benzylamine in 200 ml of acetone, and following the procedure of Example 6,B!, there were obtained 16.7 g (yield: 88%) of N-benzyl-N-methyl-4-oxo-pentanamide.