Réaction #566329

Équation de réaction

3-buten-1-ol

NaH

bromo-acetic acid

→

title compound

Rendement 126.8%

But-3-enyloxy-acetic acid

Rendement 126.8%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas then added
2. 2
   workup.WAITthe mixture kept for additional 5 min. at 0° and for 2 h at ambient temperature
3. 3
   workup.ADDITIONPouring
4. 4
   Extractionice/HCl dil., twofold extraction with AcOEt
5. 5
   Lavagewashing with brine
6. 6
   Séchagedrying over natrium sulfate and evaporation of the solvents

Mode opératoire

To 480 mg of NaH (50% in mineral oil, ˜20 mmol) in 10 ml of abs. THF was added at 0° 721 mg of 3-buten-1-ol (10 mmol) and the mixture stirred for 5 min. (H2-evolution). 1.39 g of bromo-acetic acid (10 mmol), dissolved in 10 ml of THF, was then added and the mixture kept for additional 5 min. at 0° and for 2 h at ambient temperature. Pouring onto crashed ice/HCl dil., twofold extraction with AcOEt, washing with brine, drying over natrium sulfate and evaporation of the solvents afforded 1.65 g of the title compound, contaminated with mineral oil, but sufficiently pure for the next step.

Source