Triethylamine → HCID 18398542, compound

Participants

Reaction Conditions

Reaction Steps

10.16 g (0.036 mol) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-3,4-dimethoxyphenylacetonitrile (prepared as described in Example 13.1) and 3.64 g (0.036 mol) of triethylamine are dissolved in 180 ml of tetrahydrofuran and cooled to 0-5° C. 8.52 g (0.036 mol) of diphenylphosphoryl chloride, dissolved in 70 ml of tetrahydrofuran, are added dropwise. When the addition is completed, the ice bath is removed and the solution stirred overnight at room temperature. Water and ethyl acetate are subsequently added, the organic layer is washed several times with saturated sodium chloride solution and water and dried over magnesium sulfate. Evaporation of the solvent gives 20.7 g of a viscous red oil, which is further purified by filtration over silica gel (eluent: hexane/ethyl acetate 9:1). Yield: 11.5 g (62%) (4-diphenylphosphoryloxyimino-cyclohexa-2,5-dienylidene)-3,4-dimethoxyphenyl-acetonitrile, reddish viscous oil which solidifies upon standing. 31P-NMR (CDCl3; δ relative to H3PO4 as external reference): 37.102 and 2.9.092 ppm (P(V) of the (E) and (Z)-isomers). 1H-NM R (CDCl3, δ [ppm]): 7.9-7.75 (m, 4H); 7.55-7.35 (m, 6H), 7.4-6.65 (m, 7H); 3.91/3.90 (s, 3H, (E)/(Z) isomers); 3.89/3,88 (s, 3H, (E)/(Z) isomers).

Provenance & Evidence