反应详情

温度

-25 °C

In a dry 500 ml three neck flask under nitrogen, a solution of cuprous iodide (0.28 g, 1.5 mmol) and dimethyl sulfide (8 ml) in 30 ml of dry THF was stirred at room temperature for 10 minutes. Pyridine (2.43 ml, 30 mmol) in 120 ml of dry THF was added to the reaction, then cooled to -25° C. Phenylchloroformate (3.9 ml, 30 mmol) in 10 ml dry THF was added to the reaction via an addition funnel (a thick brown precipitate formed immediately upon addition). The mixture was stirred for 15 minutes.Methyl magnesium chloride (10 ml, 30 mmol) was added to the mixture via syringe whereupon the brown precipitate dissolved. The reaction was stirred at -25° C. for 20 minutes then stirred at room temperature for 20 minutes. 20% NH4Cl(aq) (70 ml) was added to the reaction. The mixture was then extracted with 150 ml diethyl ether. The organic extract was then washed with 40 ml portions of 20% NH4 Cl(aq) /NH4OH (1:1), water, 10% HCl(aq), water, and brine.The organic layer was then dried over NaCl/Na2SO4, filtered, andconcentrated to yield 5.9 g of a yellow oil. Kugelrohr distillation (bp. 150°-170° C., 1 mmHg) to yield 4.9 g (77%) of the desired compound (A).

1. customformed immediately upon addition)
2. dissolutiondissolved
3. stirringThe reaction was stirred at -25° C. for 20 minutes
4. stirringthen stirred at room temperature for 20 minutes
5. extractionThe mixture was then extracted with 150 ml diethyl ether
6. extractionThe organic extract
7. washwas then washed with 40 ml portions of 20% NH4 Cl(aq) /NH4OH (1:1), water, 10% HCl(aq), water, and brine
8. dry with materialThe organic layer was then dried over NaCl/Na2SO4
9. filtrationfiltered