Reaktion #56737

Reaktionsgleichung

(R)-2-(2-Allyloxy-4-nitrophenoxymethyl)-oxirane

mesitylene

→

(8-Allyl-7-nitro-2,3-dihydro-benzo(1,4)dioxin-2-yl)-methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationFiltration of the black solid
2. 2
   Sonstigethat formed
3. 3
   Sonstigegave 1.5 g of very polar material
4. 4
   SonstigeEvaporation of the solvent in vacuum
5. 5
   Sonstigegave 10 g
6. 6
   Sonstigeof recovered
7. 7
   Sonstigeslowly crystallized
8. 8
   Sonstigeon recovered

Vorschrift

(R)-2-(2-Allyloxy-4-nitrophenoxymethyl)-oxirane (20 g, 80 mmoles) prepared as above was heated at 155° C. in mesitylene for 24 hours under nitrogen. Filtration of the black solid that formed gave 1.5 g of very polar material. Evaporation of the solvent in vacuum followed by column chromatography on silica gel with methylene chloride as eluent gave 10 g of recovered starting material and 7.5 g of the desired rearranged (S)-(8-allyl-7-nitro-2,3-dihydro-benzo(1,4)dioxin-2-yl)-methanol, which slowly crystallized on standing in vacuum (m.p. 67° C.). The yield based on recovered starting material is 75%.

Quelle