Reaktion #74986

Reaktionsgleichung

1[7-[(1,3-dithia-2-cyclopentyl)]-3,3-dimethyl-1,5-dioxaspiro[5,4]-dec-8-yl]-trans-1-octene-3-ol tetrahydropyranyl ether

methyl iodide

CaCO3

H2O

DMF

→

3-[3,3-Dimethyl-8[-3-pentyl-3-tetrahydropyranyloxy-trans-1-propenyl]-1,5-dioxaspiro[5,4]-dec-7-yl]-propionaldehyde

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled
2. 2
   Filtrationfiltered with suction
3. 3
   Sonstigeto remove the precipitate
4. 4
   Sonstigethe filtrate was evaporated to dryness at 0.1 mm Hg
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ether
6. 6
   Waschenwashed with H2O
7. 7
   Trocknendried over MgSO4
8. 8
   Sonstigethe solvent was removed by distillation under reduced pressure
9. 9
   SonstigeThe oily residue which was not further purified

Vorschrift

1.05 g [2.05 mmoles] of 1[7-[(1,3-dithia-2-cyclopentyl)]-3,3-dimethyl-1,5-dioxaspiro[5,4]-dec-8-yl]-trans-1-octene-3-ol-tetrahydropyranyl ether was stirred for 2 hours at 50° C. in 100 ml of DMF with 0.7 ml (10.3 mmoles) of methyl iodide, 1.4 g (14 moles) of CaCO3 and 0.4 ml of H2O. The solution was cooled, combined with 50 ml of acetone, filtered with suction to remove the precipitate and the filtrate was evaporated to dryness at 0.1 mm Hg. The residue was dissolved in ether, washed with H2O, dried over MgSO4 and the solvent was removed by distillation under reduced pressure. The oily residue which was not further purified showed in the infrared spectrum a strong carbonyl band at 1730 cm-1.

Quelle