Dimethylformamide → HCID 18404088, Verbindung
Reaktionsgleichung
C([Li])(C)(C)C.CCCCC.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].CN(C)[CH:26]=[O:27]>C1COCC1>[CH:26]([C:13]1[CH:14]=[CH:15][S:11][C:12]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:27]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
A solution of tert-butyllithium in pentane (1.7 M, 35.4 mL, 60.2 mmol, 2.40 equiv) was added to a solution of tert-butyl 2-thienylcarbamate (10-2, 5.00 g, 25.1 mmol, 1 equiv) in THF (75 mL) at −78° C., and the resulting mixture was stirred at −78° C. for 1.5 h. N,N-Dimethylformamide (5.83 mL, 75.3 mmol, 3.00 equiv) was added, and the mixture was then warmed to 0° C. The reaction mixture was partitioned between water (300 mL) and EtOAc (2×200 mL). The combined organic layers were then dried over sodium sulfate and concentrated, and the residue was purified by flash column chromatography (hexane, initially, grading to 30% hexane in EtOAc) to give tert-butyl 3-formyl-2-thienylcarbamate (10-3) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 10.51 (s, 1H), 9.80 (s, 1H), 7.11 (d, 1H, J=5.7 Hz), 6.68 (d, 1H, J=5.9 Hz), 1.55 (s, 9H).
Aufarbeitung
- temperaturethe mixture was then warmed to 0° C
- customThe reaction mixture was partitioned between water (300 mL) and EtOAc (2×200 mL)
- dry with materialThe combined organic layers were then dried over sodium sulfate
- concentrationconcentrated
- customthe residue was purified by flash column chromatography (hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-05f93067334745ba8d01bd486694bfdb
- Quelldatensatz
- uspto-grants-2002_11
- Patentnummer
- US06479512B1
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