Acetic Acid → HCID 10679379, Verbindung

A stirred solution of tetrahydro-pyran-4-one (5 g) in toluene (50 mL) was treated sequentially with cyano-acetic acid ethyl ester (5.3 mL), ammonium acetate (0.7 g), acetic acid (2.2 mL) and piperidine (3 drops) then stirred at reflux temperature for 3.5 hours and then stood at room temperature for 3 days. The reaction mixture was evaporated to give a red oil, which solidified on standing at room temperature. This solid was treated with water (30 mL) and the mixture was extracted with ethyl acetate (50 mL). The extract was washed with saturated aqueous sodium bicarbonate solution (30 mL), then with water (30 mL), then dried over magnesium sulfate and then evaporated. The residual pale yellow waxy solid (8.92 g) was refluxed with petroleum ether (b.p. 80–100° C.) when partial solution was achieved. This mixture was treated with cyclohexane (20 mL) and then decanted to remove a small amount of brown gum. The decanted solution was stood at room temperature overnight and the resulting crystalline pale yellow solid was filtered then washed with pentane and then dried at 40° C. under vacuum to give the title compound (5.10 g) as a pale yellow crystalline solid. LC-MS: RT=2.85 minutes, MS(ES+): 169(M+H)+, MS(ES−): 194(M−H)−.

1. temperatureat reflux temperature for 3.5 hours
2. customThe reaction mixture was evaporated
3. customto give a red oil, which
4. customon standing at room temperature
5. extractionthe mixture was extracted with ethyl acetate (50 mL)
6. washThe extract was washed with saturated aqueous sodium bicarbonate solution (30 mL)
7. dry with materialwith water (30 mL), then dried over magnesium sulfate
8. customevaporated
9. temperatureThe residual pale yellow waxy solid (8.92 g) was refluxed with petroleum ether (b.p. 80–100° C.) when partial solution
10. additionThis mixture was treated with cyclohexane (20 mL)
11. customdecanted
12. customto remove a small amount of brown gum
13. waitThe decanted solution was stood at room temperature overnight
14. filtrationthe resulting crystalline pale yellow solid was filtered
15. washthen washed with pentane
16. customdried at 40° C. under vacuum

ORD-Eintrag

ord-c42475c8b6564dd79e6d832b2d676b93

Quelldatensatz

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07166616B2