Water → HCID 29938143, Verbindung
Reaktionsgleichung
[H-].[Na+].[O:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH:17]=O)=[CH:16][C:11]=2[CH2:10][CH2:9]1.[OH2:19]>>[O:3]1[C:7]2[CH:13]=[CH:14][C:15](/[CH:16]=[CH:11]/[C:12]([O:8][CH2:9][CH3:10])=[O:19])=[CH:17][C:6]=2[CH2:5][CH2:4]1Komponenten
5
Versuchsvorschrift
60% sodium hydride (3.39 g, 84.6 mmols) was added to a tetrahydrofuran (150 ml) solution of triethyl phosphonoacetate (19.0 g, 84.6 mmols) while cooling with ice, and the mixture was stirred for 20 minutes. To this was dropwise added a tetrahydrofuran (15 ml) solution of 2,3-dihydrobenzofuran-5-carbaldehyde (11.4 g, 76.9 mmols) and stirred further for 1 hour. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica-gel column chromatography (hexane/ethyl acetate=from 95/5 to 9/1) to obtain 14.7 g (yield: 88%) of the target compound. This was oily.