Benzaldehyde → Methyl 3-Hydroxy-2-methylene-3-phenylpropionate

Reaktionsgleichung

N12CCC(CC1)CN2.[CH:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]>>[OH:16][CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:18](=[CH2:19])[C:17]([O:21][CH3:22])=[O:20]

Komponenten

Edukt 3

HCID 240Benzaldehyde

HCID 7294Methyl Acrylate

HCID 136165Diazabicyclo(2.2.2)octane

Produkt 1

HCID 9942369Methyl 3-Hydroxy-2-methylene-3-phenylpropionateAusbeute 77 %

Versuchsvorschrift

Diazabicyclo[2.2.2]octane (5.2 g, 0.046 mol, 0.15 eq) was added to a mixture of benzaldehyde (31.5 mL, 0.309 mol, 1 eq) and methyl acrylate (42 mL, 0.464 mol, 1.5 eq). The reaction mixture was then allowed to stir at room temperature for 7 days. The reaction mixture was purified by column chromatography (eluent:hexane/ethyl acetate=95:5) to give the desired product as colorless oil (42 g, 77%). Rf 0.5 (hexane/ethyl acetate=7:3). 1H NMR δ (DMSO-d6) 3.6 (s, 3H), 5.43 (m, 1H), 5.73 (m, 1H), 5.98 (s, 1H), 6.19 (s, 1H), 7.29 (m, 5H).