Diethyl Ether → HCID 54382316, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl N,N-diisopropylacetamide phosphonate (8.4 g, 30 mmol) in THF (20 mL) was added dropwise to sodium hydride (80%, 0.85 g, 29 mmol) during 30 min, keeping the temperature below 30° C. A solution of 2-trifluoromethyl-benzophenone (5.0 g, 20 mmol) in THF (20 mL) was added and the reaction mixture was heated to 50° C. and kept at that temperature for 16 h. A second portion of the phosphorous ylide (15 mmol), prepared as above, was added. After another 24 h at 50° C. the mixture was partioned between diethyl ether and water. The etheral layer was evaporated and the residue chromatographed on silica (toluene-ethyl acetate 9:1) yielding 3.0 g (41%) as a mixture of the E- and Z-isomers. Labels a and b refer to the different isomers. 1H NMR (CDCl3-d) δ0.80 (d, 6Ha), 1.08 (d, 3Hb), 1.24 (t, 6Hb), 1.31 (d, 3Hb), 1.44 (d, 6Ha), 3.32 (m, 1Ha), 3.34 (m, 1Hb), 4.19 (m, 1Hb), 4.32 (m, 1Ha), 6.04 (s, 1Ha), 6.65 (s, 1Hb) and 7.18-7.75 (m, 9Ha, 9Hb).

Provenance & Evidence