Réaction #48328

Équation de réaction

Methylcyclobutanone

THF

allylmagnesium bromide

water

→

1-Allyl-3-methylcyclobutanol

Rendement 46.9%

Conditions de réaction

Traitement

1. 1
   Extractionextracted
2. 2
   SéchageThe combined organic extracts were dried over MgSO4
3. 3
   Autreevaporated
4. 4
   Autrepurified via glass col

Mode opératoire

Methylcyclobutanone (3.200 g, 38.043 mmol) was dissolved in 200 ml THF and allylmagnesium bromide (190.21 ml, 190.21 mmol) was added in one portion. The mixture was stirred for 4 h at RT, hydrolyzed with water and extracted. The combined organic extracts were dried over MgSO4 and evaporated and purified via glass col. Chrom. (25-75% hex. in EtOAc). 1-Allyl-3-methylcyclobutanol (2.250 g, 46.9% yield) was obtained as a mixture of cis-trans isomers approx 4:1 (where the major compound is the one Me-cis to OH) based on NMR.

Source