Reaktion #8401

Reaktionsgleichung

Diazabicyclo[2.2.2]octane

benzaldehyde

methyl acrylate

→

desired product

Ausbeute 77.0%

(±)Methyl 3-hydroxy-2-methylene-3-phenylpropanoate

Ausbeute 77.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was purified by column chromatography (eluent:hexane/ethyl acetate=95:5)

Vorschrift

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).

Quelle