Sodium Bicarbonate → 4-(5-Hydroxy-2-oxo-3-propionyl-2-H-pyran-6-yl)pentanol
Reaktionsgleichung
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:14]1[O:19][C:18](=[O:20])[C:17]([C:21](=[O:24])[CH2:22][CH3:23])=[C:16](O)[CH:15]=1)[CH3:13])(C(C)(C)C)(C)C.C([O-])(O)=[O:27].[Na+]>CC(O)=O.C1COCC1.O>[OH:27][C:15]1[CH:16]=[C:17]([C:21](=[O:24])[CH2:22][CH3:23])[C:18](=[O:20])[O:19][C:14]=1[CH:12]([CH3:13])[CH2:11][CH2:10][CH2:9][OH:8]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
6-(5-(t-Butyldimethylsilyloxy)pentan-2-yl)-4-hydroxy-3-propionyl-2-H-pyran-2-one (IV; 3 g; 8.15 mmol) in 100 ml AcOH/THF/water (3/1/1, v/v/v) was stirred for 18 h at 25° C. The reaction mixture was neutralized with saturated NaHCO3, extracted with 3×50 ml EtOAc, dried with anhydrous Na2SO4, and evaporated to an oil. The product was purified via silica chromatography (40% EtOAc in hexanes).