Réaction #80852

Équation de réaction

3-buten-1-ol

pyridine

tert-butyldimethylsilyl chloride

→

product

Rendement 56.3%

4-[(tert-Butyldimethylsilyl)oxy]-1-butene

Rendement 56.3%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   AutreThe ice-bath was removed
2. 2
   workup.ADDITIONThe mixture, containing a white precipitate
3. 3
   workup.ADDITIONwas poured into water (60 mL)
4. 4
   workup.STIRRINGshaken
5. 5
   AutreThe methylene chloride layer was separated from the aqueous layer
6. 6
   Extractionthe aqueous layer extracted with methylene chloride (30 mL)
7. 7
   Lavagewashed twice with water
8. 8
   Séchagedried (Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Autreevaporated
11. 11
    Autreto give 8.94 g of crude product
12. 12
    workup.DISTILLATIONVacuum distillation
13. 13
    Autreafforded several fractions
14. 14
    Autrethe fraction with bp 80°-82° C. at 35 mm Hg was collected

Mode opératoire

Under a nitrogen atmosphere, to a cold (0° C.), stirring solution of 3-buten-1-ol (2.16 g, 30.0 mmol), pyridine (9 mL), and methylene chloride (30 mL) was added tert-butyldimethylsilyl chloride (4.53 g, 30.1 mmol) purchased from Aldrich Chemical Company. The ice-bath was removed and the mixture was allowed to stir 1 h at room temperature. The mixture, containing a white precipitate, was poured into water (60 mL) and shaken. The methylene chloride layer was separated from the aqueous layer, and the aqueous layer extracted with methylene chloride (30 mL). The two resulting organic extracts were combined, washed twice with water, dried (Na2SO4), filtered, and evaporated to give 8.94 g of crude product. Vacuum distillation afforded several fractions, the fraction with bp 80°-82° C. at 35 mm Hg was collected to give 3.14 g (56.3%) of product as an oil. 1H NMR (CDCl3): δ 5.86-5.73 (m, 1H), 5.08-4.98 (m, 2H), 3.64 (t, 2H), 2.29-2.22 (m, 2H), 0.87 (s, 9H), 0.03 (s, 6H).

Source