Reaktion #1186198

Reaktionsgleichung

2-phenylacrylic acid methyl ester

mCPBA

→

title compound

2-Phenyloxirane-2-carboxylic Acid Methyl Ester

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe title compound was synthesized
2. 2
   FiltrationThe reaction mixture was then filtered
3. 3
   Waschenthe solid was washed with methylene chloride
4. 4
   WaschenThe filtrate was washed three times with 50 ml of equal parts solution
5. 5
   WaschenThe organic layer was washed with water and brine
6. 6
   Trocknendried over MgSO4
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

The title compound was synthesized according to a literature method (Whitman Tetrahedron 1985, 41, 1183). To a mixture of 2-phenylacrylic acid methyl ester (7.92 g, 45 mmol) in 60 ml of methylene chloride was added mCPBA (13.1 g, 58.5 mmol) and the reaction was stirred at 45° C. overnight. The reaction mixture was then filtered and the solid was washed with methylene chloride. The filtrate was washed three times with 50 ml of equal parts solution consisting of saturated Na2S2O3 and saturated NaHCO3. The organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure to afford the title compound in greater than 95% purity according to 1H NMR (85% yield). 1H NMR (CDCl3, 300 MHz) δ: 7.50-7.30 (m, 5H), 4.22 (q, J=7.2 Hz, 2H), 3.40 (d, J,=7.1 Hz, 1H), 2.95 (d, J=7.1 Hz, 1H), 1.26 (t, J=7.2 Hz, 3H) ppm.

Quelle