Réaction #722180

Équation de réaction

2,6,6-Trimethyl-10-(tetrahydro-pyran-2-yloxy)-dec-3-yn-2-ol

methanol

pyridinium-(toluene-4-sulfonate)

→

title compound

(10E,12Z)-(S)-12-(5-Hydroxy-2-methylene-cyclohexylidene)-6,6-dimethyl-2-methyl-dodec-10-en-3-yn-2-ol

Conditions de réaction

Traitement

1. 1
   workup.WAITkept at room temperature for 1 night
2. 2
   workup.ADDITIONThe reaction mixture was then poured
3. 3
   Extractionextracted twice with ethylacetate
4. 4
   Lavagewashed with brine
5. 5
   Séchagedried over sodium sulfate
6. 6
   Autreevaporated to dryness

Mode opératoire

609 mg of 2,6,6-Trimethyl-10-(tetrahydro-pyran-2-yloxy)-dec-3-yn-2-ol (2.05 mmol) was dissolved in 13.5 ml of methanol, treated with 76 mg of pyridinium-(toluene-4-sulfonate) (0.15 eq.), and kept at room temperature for 1 night. The reaction mixture was then poured onto crushed ice/Na2CO3, extracted twice with ethylacetate, washed with brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/ethylacetate=7/3) produced 413 mg of the title compound as yellowish oil.

Source