반응 #76188

반응 방정식

toluene

potassium carbonate

2-(5-Methyl-2-phenyl-4-oxazolyl)ethyl methanesulfonate

2-(5-methyl-2-phenyl-4-oxazolyl)ethyl methanesulfonate

compound [ 7 ]

2-(5-methyl-2-phenyl-4-oxazolyl)ethyl methanesulfonate

dimethyl 2-(4-hydroxybenzylidene)-malonate

compound [ 8 ]

dimethyl 2-(4-hydroxybenzylidene)malonate

→

title compound

수율 85.0%

dimethyl [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene]-malonate

수율 85.0%

용매

water

반응 조건

후처리

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   온도cooled
3. 3
   workup.STIRRINGby stirring
4. 4
   기타the aqueous layer was removed
5. 5
   workup.ADDITION10% aqueous sodium chloride solution (210 mL) was added to the organic layer
6. 6
   workup.STIRRINGwith stirring
7. 7
   기타the aqueous layer was removed
8. 8
   농축The organic layer was concentrated
9. 9
   workup.DISSOLUTIONthe concentrated residue was dissolved in methanol (150 mL)
10. 10
    온도under heating
11. 11
    온도The reaction mixture was cooled to 10° C. or less
12. 12
    workup.STIRRINGthe reaction mixture was stirred for 1 hr
13. 13
    여과The obtained crystals were collected by filtration
14. 14
    세척washed with methanol (65 mL)

실험 절차

2-(5-Methyl-2-phenyl-4-oxazolyl)ethyl methanesulfonate obtained in Example 4 (compound [7]; 24.4 g) and dimethyl 2-(4-hydroxybenzylidene)-malonate obtained in Preparation Example 1 (compound [8]; 20.5 g) were mixed with tetrabutylammonium bromide (1.4 g) and toluene (210 mL). The mixture was heated to 90° C. and dissolved. Then potassium carbonate (13.2 g) was added and the mixture was stirred at 110° C. for 6 hr. The reaction mixture was ice-cooled and water (210 mL) was added, which was followed by stirring. After standing still, the aqueous layer was removed and 10% aqueous sodium chloride solution (210 mL) was added to the organic layer with stirring. The reaction mixture was allowed to stand and the aqueous layer was removed. The organic layer was concentrated and the concentrated residue was dissolved in methanol (150 mL) under heating. The reaction mixture was cooled to 10° C. or less and the reaction mixture was stirred for 1 hr. The obtained crystals were collected by filtration and washed with methanol (65 mL) to give the title compound (compound [9]; 31.1 g, yield 85.0%).

출처