Tetrahydrofuran → (E)-Ethyl 3-cyclohexylacrylate

Temperature

-78 °C

Add triethylphospinoacetate (185 g, 821 mmol) to a suspension of hexane-washed sodium hydride (34.5 g, 60%, 862 mmol) in THF (1 L) at 0° C. Stir the resulting mixture for 1 h, and then cool it to −78° C. Then add a solution of cyclohexylmethanal (92.2 g, 821 mmol) in THF (500 mL) dropwise over 90 min, maintaining an internal temperature of less than −68° C. Allow the reaction mixture to warm to r.t. over 18 h. Then add a solution of saturated aqueous ammonium chloride solution (1 L) to the reaction mixture carefully. Extract the resulting mixture with ether (3×1 L). Combine the extracts and wash them with water (2×1 L), followed by saturated aqueous sodium chloride solution (1 L). Then dry the extracts over magnesium sulfate, and concentrate the solution under vacuum to afford the title compound as a yellow oil (154.8 g). GC-MS (m/e): 182 (M+).

1. temperaturemaintaining an internal temperature of less than −68° C
2. temperatureto warm to r.t. over 18 h
3. extractionExtract the resulting mixture with ether (3×1 L)
4. washCombine the extracts and wash them with water (2×1 L)
5. dry with materialThen dry the extracts over magnesium sulfate
6. concentrationconcentrate the solution under vacuum

ORD record

ord-b90066380cb94604bad88b4cf3df3718

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576108B2