반응 #56737

반응 방정식

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

mesitylene

→

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

반응 조건

후처리

1. 1
   여과Filtration of the black solid
2. 2
   기타that formed
3. 3
   기타gave 1.5 g of very polar material
4. 4
   기타Evaporation of the solvent in vacuum
5. 5
   기타gave 10 g
6. 6
   기타of recovered
7. 7
   기타slowly crystallized
8. 8
   기타on recovered

실험 절차

(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%.

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