反应详情

To a suspension of sodium hydride (0.487 g, 12.17 mmol, 60% in mineral oil) in DMSO (33.8 ml) stirring under nitrogen was added trimethyl sulfoxonium iodide (2.68 g, 12.17 mmol) in 4 portions over 20 minutes. A solution of 3,4-bis(benzyloxy)-6-(1-phenylethenyl)pyridazine (Intermediate 25; 3.2 g, 8.11 mmol) in tetrahydrofuran (50.7 ml) was added via a dropping funnel over 90 minutes before the reaction was left to stir at room temperature for 18 hours. The resulting mixture was concentrated, poured into ice water and extracted with ethyl acetate (×3). The organics portion was dried (MgSO4), filtered and concentrated to give a brown oil. The crude oil was purified by silica chromatography (eluting with 0-50% ethyl acetate in petrol) to yield 3,4-bis(benzyloxy)-6-(1-phenylcyclopropyl)pyridazine as a yellow oil (yield=23%).

1. waitwas left
2. stirringto stir at room temperature for 18 hours
3. concentrationThe resulting mixture was concentrated
4. additionpoured into ice water
5. extractionextracted with ethyl acetate (×3)
6. dry with materialThe organics portion was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customto give a brown oil
10. customThe crude oil was purified by silica chromatography (eluting with 0-50% ethyl acetate in petrol)