1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol → 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-one
Reaktionsgleichung
[C:1]1([CH:7]([OH:18])[C:8]#[C:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl>[C:1]1([C:7](=[O:18])[C:8]#[C:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol (3.0 g, 12.2 mmol) in DCM (50 mL) was added DMP (10.0 g, 24.4 mmol). The resulting solution was stirred for 30 min at room temperature and then the reaction mixture was poured into NaHCO3/NaS2O3 solution and stirred for overnight, extracted with DCM (3×150 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give a residue. The residue was purified by silica gel column chromatography (3% ethyl acetate in petroleum ether) to afford 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-one as a light yellow oil (2.4 g).