Reaktionsgleichung
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=[O:21])[O:3]1.[OH-].[Na+].Cl>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8]([CH:7]=[C:5]([OH:6])[C:4]([OH:21])=[O:3])=[O:9])=[CH:15][CH:16]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide (3.65 g, 11.8 mmol) in tetrahydrofuran (150 ml) was treated at 15° C. with 35 ml (35 mmol) of 1 M aqueous sodium hydroxide. After 30 minutes, the reaction mixture was acidified with 1N hydrochloric acid (65 ml) and extracted with ethyl acetate. The organic phase was washed with brine, dried (magnesium sulfate) and evaporated in vacuo to give a white solid. Recrystallization from ethyl acetate and hexane gave 3.04 g (96% yield) of the title material as white needles; mp 129° C. (dec.). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.73 (3H, s), 4.84 (2H, s), 6.57 (1H, s), 7.07 (2H, mn), 7.34 (2H, m). 13CNMR (enol form) 125 MHz (DMSO-d6) δ (ppm): 47.08, 63.05, 93.35, 130.61, 130.83, 130.90, 132.86, 132.89, 133.14, 133.16, 161.02, 161.38, 163.32, 163.81, 170.97. Anal. calcd for C12H12FNO5: C, 53.53; H, 4.49; N, 5.20; Found: C, 53.78; H, 4.30; N, 4.90.
Aufarbeitung
- extractionextracted with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried (magnesium sulfate)
- customevaporated in vacuo
- customto give a white solid
- customRecrystallization from ethyl acetate and hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-8b5ec6c7b3f14e7c927ded3eef64d733
- Quelldatensatz
- uspto-grants-2004_08
- Patentnummer
- US06777440B2
Verknüpfte Notizen
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