Triethylamine → Decanoic acid, 2,5-dioxo-1-pyrrolidinyl ester

A solution of decanoyl chloride (5.0 g) in tetrahydrofuran (20 ml) was dropwise added to a mixture of N-hydroxysuccinimide (3.06 g) and triethylamine (3.7 ml) in tetrahydrofuran (30 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for one hour and then at ambient temperature for 15 hours. A precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 ml). The solution was washed with water (50 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give N-decanoyloxysuccinimide as a crystal (4.95 g).

1. temperaturecooling
2. stirringThe mixture was stirred at the same temperature for one hour
3. filtrationA precipitate was filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
6. washThe solution was washed with water (50 ml)
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was crystallized from ethyl acetate-hexane

ORD record

ord-df0fac4af2d24512bf029bda2b199db5

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04554269