Réaction #531597

Équation de réaction

HCl

NH4Cl

Trimethylsilyl 3-butynyl ether

ether pentane

dimethyl sulfide

→

7-methyl-3-methylene-7-octen-1ol

Solvants

ether

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting solution is cooled to -60°
2. 2
   workup.ADDITIONanother 14 ml of dimethyl suflide is added
3. 3
   workup.DISSOLUTIONto dissolve the precipitate that forms
4. 4
   Températureto warm to -25°
5. 5
   workup.STIRRINGwith stirring for several hours
6. 6
   workup.ADDITIONThe reaction is then poured into
7. 7
   Autreto warn to RT
8. 8
   workup.STIRRINGstirred overnight
9. 9
   ExtractionThe reaction is worked up by water and extraction with ether (2×)
10. 10
    Lavagewashed with sat (NH4)2SO4, water and brine
11. 11
    Filtrationfiltered
12. 12
    Autresolvent removed

Mode opératoire

2.1 Grams (10.0 mmol) of the above complex is suspended in 15 ml of dry ether, and 12 ml of dimethyl sulfide is added under nitrogen. The resulting solution is cooled to -60° and another 14 ml of dimethyl suflide is added to dissolve the precipitate that forms. The Grignard reagent (24 ml, 9.6 mmol) from B above is added at -60° over 5 min and the reaction is stirred at -45° for 2 hr. Trimethylsilyl 3-butynyl ether (1.4 g, 9.8 mmol) (preparation follows) in ether/pentane (5 ml/30 ml) is added at -45°; the mixture is allowed to warm to -25° with stirring for several hours. The reaction is then poured into a pre-cooled (<-10°) solution of HCl/sat. NH4Cl, allowed to warn to RT and stirred overnight. The reaction is worked up by water and extraction with ether (2×). The ether phases are combined, washed with sat (NH4)2SO4, water and brine, filtered and solvent removed to give 7-methyl-3-methylene-7-octen-1ol.

Source