Reaktion #633899

Reaktionsgleichung

Cerium chloride heptahydrate

sodium iodide

methyl 3-hydroxy-7-methyl-6-octenoate

→

title compound

methyl 2-(6,6-dimethyltetrahydropyran-2-yl)acetate

Lösungsmittel

—

Heterocycles

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeobtained by the method
2. 2
   Temperaturunder reflux for 10 hours
3. 3
   workup.WAITThe reaction solution was left
4. 4
   Temperaturto cool
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   workup.ADDITIONDiethyl ether and 12 ml of 1 N hydrochloric acid were added to the resulting residue
7. 7
   Sonstigethe organic layer was separated
8. 8
   workup.ADDITIONDiethyl ether was added to the aqueous layer
9. 9
   Sonstigethe organic layer was separated
10. 10
    WaschenThe combined organic layers were sequentially washed with water
11. 11
    Trocknena saturated sodium bicarbonate solution (pH=9), a 5% sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate
12. 12
    Einengenconcentrated under reduced pressure
13. 13
    SonstigeThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Vorschrift

Cerium chloride heptahydrate (812 mg) and sodium iodide (327 mg) were added to a solution of methyl 3-hydroxy-7-methyl-6-octenoate obtained by the method described in Heterocycles, 34, 1107-1117 (1992) (4.06 g) in acetonitrile (10 ml), and the reaction solution was heated under reflux for 10 hours. The reaction solution was left to cool and then concentrated under reduced pressure. Diethyl ether and 12 ml of 1 N hydrochloric acid were added to the resulting residue, and the organic layer was separated. Diethyl ether was added to the aqueous layer, and the organic layer was separated. The combined organic layers were sequentially washed with water, a saturated sodium bicarbonate solution (pH=9), a 5% sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 2.65 g of the title compound. The property values of the compound are as follows.

Quelle