반응 #1069836

반응 방정식

of(R)-N-acryloyl-N-allyloxyalanine benzyl ester

(R)-N-Acryloyl-N-allyloxyalanine benzyl ester

→

olefin

(R)-2-(3-Oxo-3,6-dihydro-[1,2]oxazin-2-yl)-propionic acid benzyl ester

용매

CH2Cl2

반응 조건

후처리

1. 1
   세척by washing with CH2Cl2 (50 mL)
2. 2
   기타After removal of the solvent
3. 3
   기타the dark oily residue was purified
4. 4
   건조by dry flash chromatography (Silica Gel 60H for TLC, 5% EtOAc-hexanes→15% EtOAc-hexanes)

실험 절차

A solution of(R)-N-acryloyl-N-allyloxyalanine benzyl ester (6a) (7.32 g, 25.3 mmol) and bis(tricyclohexylphosphine)benzylidene ruthenium dichloride (Grubb's catalyst) (1.04 g, 1.26 mmol, 5 mol %) in dry CH2Cl2 (250 mL) was refluxed with Silica Gel 60H (for TLC) followed by washing with CH2Cl2 (50 mL). After removal of the solvent, the dark oily residue was purified by dry flash chromatography (Silica Gel 60H for TLC, 5% EtOAc-hexanes→15% EtOAc-hexanes) to afford 6.05 g (92%) the olefin 7a identical to that described above.

출처