Water → Ethyl 3-oxa-8-nonynoate

To a solution of 5-hexyn-1-ol (2.0 g, 20.4 mmol) in N,N-dimethylformamide (40 ml) was added sodium hydride (815 g, 60% in oil, 20.41 mmol) at 0° C. The mixture was stirred for 1 hour, and ethyl bromoacetate (3.4 ml, 30.5 mmol) was added thereto. The mixture was stirred at the same temperature for 1 hour. After the reaction was completed, water was added thereto. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The organic solvent was removed under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (1.38 g, yield: 37%).

1. stirringThe mixture was stirred at the same temperature for 1 hour
2. extractionThe resulting mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated saline solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customThe organic solvent was removed under reduced pressure
7. customto give a crude product
8. customThis crude product thus obtained

ORD-Eintrag

ord-53026435b997496fbc94e942803c281e

Quelldatensatz

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07074819B2