Reaktion #81637

Reaktionsgleichung

Maleic anhydride

(S)-(+)-2-phenylglycinol

EtOAc HOAc

→

title compound

(S)-1-[2-(Acetyloxy)-1-phenylethyl]-2,5-dihydro-1H-pyrrol-2,5-dione

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA precipitate formed immediately
2. 2
   workup.DISSOLUTIONredissolved after 1 hr
3. 3
   workup.STIRRINGThe mixture was stirred overnight
4. 4
   SonstigeThe THF was evaporated
5. 5
   workup.DISSOLUTIONthe residue was dissolved in 6 ml hot CH2Cl2
6. 6
   SonstigeCrystals formed almost immediately in the hot mixture which
7. 7
   Sonstigeat 5°
8. 8
   Sonstigefor 2 hrs
9. 9
   FiltrationThe crystals were filtered
10. 10
    Waschenwashed with cold CH2Cl2
11. 11
    Sonstigedried under vacuum

Vorschrift

Maleic anhydride (358 mg, 3.65 mM) was added to (S)-(+)-2-phenylglycinol (500 mg, 3.65 mM) dissolved in 5 ml THF stirred under Ar. A precipitate formed immediately but redissolved after 1 hr. The mixture was stirred overnight. TLC (silica gel, EtOAc/HOAc 95:5) showed two spots, the product Rf 0.34, and a lower Rf spot, Rf 0.09. The THF was evaporated, and the residue was dissolved in 6 ml hot CH2Cl2. Crystals formed almost immediately in the hot mixture which was let stand at 5° for 2 hrs. The crystals were filtered, washed with cold CH2Cl2, and dried under vacuum to give the title compound: 600 mg (70%), mp. 131°-2°. ##STR48##

Quelle