반응 #4599

반응 방정식

morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

pyridine

phosgene

→

morpholinoethyl (E)-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

용매

benzene

benzene

반응 조건

후처리

1. 1
   여과the precipitate filtered off
2. 2
   기타solvent removed from the filtrate under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue is dissolved in 5 ml of tetrahydrofuran and to this solution
4. 4
   workup.ADDITIONis added dropwise a solution of ammonia in tetrahydrofuran until the reaction
5. 5
   workup.ADDITIONThe mixture is poured into water
6. 6
   추출extracted with ethyl acetate
7. 7
   건조The organic solution is dried over magnesium sulfate
8. 8
   기타evaporated to an oil which
9. 9
   기타is chromatographed on silica gel
10. 10
    세척eluting with a 50:1 mixture of dichloromethane and methanol
11. 11
    workup.STIRRINGThe purified product is stirred with a mixture of ether and hexane
12. 12
    여과filtered

실험 절차

To a solution of 500 mgs of morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate in 10 ml of benzene cooled in an ice bath is added 0.1 ml of pyridine and 6 ml of a 12.5% solution of phosgene in benzene. The solution is stirred at 25° C. overnight, the precipitate filtered off and solvent removed from the filtrate under reduced pressure. The residue is dissolved in 5 ml of tetrahydrofuran and to this solution is added dropwise a solution of ammonia in tetrahydrofuran until the reaction is complete. The mixture is poured into water and extracted with ethyl acetate. The organic solution is dried over magnesium sulfate and evaporated to an oil which is chromatographed on silica gel, eluting with a 50:1 mixture of dichloromethane and methanol. The purified product is stirred with a mixture of ether and hexane and filtered giving morpholinoethyl (E)-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate.

출처