Reaktionsgleichung
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][CH:20]=[CH:19][C:18]=2[C:22]=1[C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.CN(C)[CH:30]=[O:31]>>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([CH:30]=[O:31])=[CH:19][C:18]=2[C:22]=1[C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Komponenten
Versuchsvorschrift
Phosphorus oxychloride (26.2 ml, 0.29 mol) was added dropwise to N,N-dimethylformamide (17 ml, 0.22 mol) under ice cooling; subsequently, a solution of 5-benzyloxy-4-tert-butylbenzofuran (40 g, 0.14 mol) in N,N-dimethylformamide (10 ml) was added dropwise. The mixture was stirred first at room temperature for 20 min, then under heating at 80° C. for 2 h. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-benzyloxy-4- tert-butyl-2-formylbenzofuran [16.2 g (yield, 36%)].
Aufarbeitung
- temperatureunder heating at 80° C. for 2 h
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-694679aed08440d89513cd51410f0c53
- Quelldatensatz
- uspto-grants-1997_02
- Patentnummer
- US05606089
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