Reacción #345809

Ecuación de reacción

7-[8-nitromethyl-7-(3-methyl-3-hydroxy-1-octenyl)-1,4-dioxaspiro[4.4]non-6-yl]-5-heptenoic acid

tetrahydrofuran

hydrochloric acid

→

title product

7-[2-(3-Hydroxy-3-Methyl-1-Octenyl)-3-Nitromethyl-5-Oxocyclopentyl]-5-Heptenoic Acid

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ether
2. 2
   LavadoAfter washing with water
3. 3
   Secadodrying over magnesium sulfate
4. 4
   Otrothe extract was evaporated
5. 5
   Otrothe residue chromatographed on silica
6. 6
   LavadoElution with 15% ethyl acetate in hexane
7. 7
   Otrogave 0.11 g

Procedimiento

A solution of 0.20 g. of 7-[8-nitromethyl-7-(3-methyl-3-hydroxy-1-octenyl)-1,4-dioxaspiro[4.4]non-6-yl]-5-heptenoic acid in 4 ml. of tetrahydrofuran was treated at 0° C. with 0.4 ml. of concentrated hydrochloric acid and stirred at 0° C. for 1.5 hours. The reaction mixture was added to water and extracted with ether. After washing with water and drying over magnesium sulfate, the extract was evaporated and the residue chromatographed on silica. Elution with 15% ethyl acetate in hexane gave 0.11 g. of the title product as an oil, λmaxfilm 3.00 (shoulder), 3.50, 5.80, 6.45, 7.25, 10.30 μ. NMR: δ 1.32 (S, 15-methyl), 4.49 (M, 2, --CH2NO2), 5.80 (M, 4, olefinic --H), 5.92 (S, 2, OH) ppm. Mass spectrum: M+ --H2O at m/e 391.2402 (theory 391.2358).

Fuente