反应详情

A solution of sodium methoxide (made from 1.43 g of sodium in dry methanol (20 ml) was added dropwise to a stirred solution of 2-(3-chlorophenyl)propanal (10.4 g) and methyl dichloroacetate (6.4 ml) in diethyl ether (30 ml) at 0° C. under nitrogen. After 1 h the mixture was quenched with brine and the product extracted into diethyl ether. The organic phase was collected, dried (MgSO4) and evaporated under reduced pressure to leave a yellow oil. The oil and thiourea (4.72 g) were dissolved in methanol (40 ml) and the mixture set at reflux for 4 h. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was separated, washed with water, collected, dried (MgSO4) and solvent evaporated under reduced pressure to leave a brown solid. The solid was triturated with isohexane and ethyl acetate mixtures and filtered to leave the subtitle product.

1. customAfter 1 h the mixture was quenched with brine
2. extractionthe product extracted into diethyl ether
3. customThe organic phase was collected
4. dry with materialdried (MgSO4)
5. customevaporated under reduced pressure
6. customto leave a yellow oil
7. temperatureat reflux for 4 h
8. customThe solvent was removed under reduced pressure
9. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
10. customThe organic phase was separated
11. washwashed with water
12. customcollected
13. dry with materialdried (MgSO4) and solvent
14. customevaporated under reduced pressure
15. customto leave a brown solid
16. customThe solid was triturated with isohexane and ethyl acetate mixtures
17. filtrationfiltered