反应详情

温度

118 °C

2-(2,4-dichloro-benzylidene)-malononitrile (95 mg, 0.4 mmol), chroman-4-one (59 mg, 0.4 mmol), ammonium acetate (78 mg, 1.2 mmol), and toluene (4 ml) were placed in a reaction vial and shaken overnight at 118° C. Upon cooling and filtration, the solution was evaporated in a vacuum zentrifuge (45° C.) and the residue was purified by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA (aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min). The obtained solid (28 mg) was dissolved in THF (1 ml) and added, under an atmosphere of Argon, to a cooled (0° C.) suspension of 100 mg of Lithium aluminum hydride in 1 ml THF in a reaction vial. The reaction mixture was shaken first for 2 h at r.t. and subsequently for 4 h at 40° C. Upon cooling, water was added carefully and the mixture was filtered. The filtrate was evaporated in a vacuum zentrifuge (45° C.). Purification of the re-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min) gave 11 mg (7%) of the title compound, MS: m/e=371.9 (M+H+), as a solid.

1. temperatureUpon cooling
2. filtrationfiltration
3. customthe solution was evaporated in a vacuum zentrifuge (45° C.)
4. customthe residue was purified by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA (aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min)
5. dissolutionThe obtained solid (28 mg) was dissolved in THF (1 ml)
6. additionadded, under an atmosphere of Argon
7. temperatureto a cooled
8. addition(0° C.) suspension of 100 mg of Lithium aluminum hydride in 1 ml THF in a reaction vial
9. stirringThe reaction mixture was shaken first for 2 h at r.t. and subsequently for 4 h at 40° C
10. temperatureUpon cooling
11. additionwater was added carefully
12. filtrationthe mixture was filtered
13. customThe filtrate was evaporated in a vacuum zentrifuge (45° C.)
14. customPurification of the
15. dissolutionre-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min)