Réaction #438979

Équation de réaction

n-butyl lithium

2-(3,4,4-trifluoro-3-butenylthio)oxazole

bromomethyl methyl ether

ammonium chloride

→

5-methoxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole

Rendement 13.2%

Solvants

ether

ether

Conditions de réaction

Traitement

1. 1
   Autreback to room temperature
2. 2
   workup.STIRRINGstirring for 1 hour
3. 3
   Autreto separate it into an ether layer
4. 4
   ExtractionThe aqueous layer was further extracted with ether and together with the separated ether layer it
5. 5
   Lavagewas washed with a saturated sodium chloride water
6. 6
   Séchagedried with anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONAfter the solvent was distilled off under reduced pressure
8. 8
   workup.ADDITIONthe residue was treated by column chromatography

Mode opératoire

10.40 ml of n-butyl lithium (1.6 M n-hexane solution) were slowly added dropwise to a solution of 3.14 g of 2-(3,4,4-trifluoro-3-butenylthio)oxazole in 40 ml of ether at −70° C. After stirring for 1 hour, a solution of 2.06 g bromomethyl methyl ether in 10 ml ether was added dropwise. After bringing the mixture back to room temperature and stirring for 1 hour, 50 ml of saturated solution of ammonium chloride was added to separate it into an ether layer and an aqueous layer. The aqueous layer was further extracted with ether and together with the separated ether layer it was washed with a saturated sodium chloride water and dried with anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was treated by column chromatography to obtain 0.5 g of 5-methoxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole (yield 13%). n20D=1.4705.

Source