反应详情

Oxalyl chloride (0.508 ml) and N,N-dimethylformamide (catalytic amount) were added to a solution of 6-oxo-6-phenylhexanoic acid (1.00 g) in tetrahydrofuran (15 ml) at room temperature, which was stirred at room temperature for 1 hour and concentrated. The residue was dissolved in ethyl acetate (25 ml) and added dropwise to a stirred mixture of 25% aqueous ammonia (20 ml) and ethyl acetate (25 ml) at 0° C. After stirring at room temperature for 2 hours water (200 ml) was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 6-oxo-6-phenylhexanamide (885 mg, yield 89%) as colorless crystals. m.p. 113-114° C.

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in ethyl acetate (25 ml)
3. additionadded dropwise to a stirred mixture of 25% aqueous ammonia (20 ml) and ethyl acetate (25 ml) at 0° C
4. stirringAfter stirring at room temperature for 2 hours water (200 ml)
5. additionwas added
6. extractionextracted with ethyl acetate
7. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
8. dry with materialdried (MgSO4)
9. concentrationconcentrated
10. customThe remaining crystals were recrystallized from ethyl acetate-hexane