반응 #927282

반응 방정식

4,5-epoxy-17-methyl-3-trifluoromethanesulfonyloxymorphinan-6-one

vinyltributyltin

LiCl

triphenylphosphine

→

NH4OH

title product

수율 155.2%

4,5-Epoxy-17-methyl-3-vinylmorphinan-6-one

수율 155.2%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONit was poured onto water
2. 2
   추출the aqueous phase was extracted with AcOEt
3. 3
   건조The organic phase was dried over Na2SO4
4. 4
   기타the solvent was removed in vacuo
5. 5
   기타The crude reaction mixture
6. 6
   기타was purified by flash chromatography
7. 7
   세척eluting with a mixture CH2Cl2/MeOH/conc

실험 절차

2 g (4.8 mmol) of 4,5-epoxy-17-methyl-3-trifluoromethanesulfonyloxymorphinan-6-one were dissolved, under a nitrogen atmosphere, in 25 ml of dimethylformamide, then 1.46 ml (5 mmol) of vinyltributyltin, 1.6 g (38.4 mmol) of LiCl, 0.337 g (0.48 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.5 g (1.9 mmol) of triphenylphosphine were added. The reaction mixture was heated to 100° C. for 3 h, then it was poured onto water and the aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2/MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 1.1 g of the title product.

출처