Réaction #160489

Équation de réaction

homopropargyl alcohol

tert-butyldimethylsilyl chloride

triethylamine

→

title compound

tert-Butyl(but-3-ynyloxy)dimethylsilane

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   LavageThe mixture was washed with water
2. 2
   Séchagethe organic layer was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate was concentrated under reduced pressure
5. 5
   Autrethe residue was purified by chromatography (95:5 hexane/ethyl acetate)

Mode opératoire

A stirred, 0° C. solution of homopropargyl alcohol (10 g, 0.14 mol) and tert-butyldimethylsilyl chloride (21.5 g, 0.14 mol) in dichloromethane (50 mL) was treated with triethylamine (22.8 mL, 0.168 mol). The mixture was then stirred overnight at room temperature. The mixture was washed with water and the organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography (95:5 hexane/ethyl acetate) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 0.08 (s, 6H), 0.90 (s, 9H), 1.96 (t, J=3 Hz, 1H), 2.41 (dt, J=6 Hz, J=3 Hz, 2H), 3.75 (d, J=6 Hz, 2H).

Source