Réaction #48331

Équation de réaction

3-(Benzyloxy)cyclobutanone Methylsulfinyl(methylthio)methane

n-Butyllithium

water

1-((1,3-dibromopropan-2-yloxy)methyl)benzene

→

3-(benzyloxy)cyclobutanone

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThe mixture was cooled down to −78° C.
3. 3
   workup.STIRRINGThe reaction was stirred over night
4. 4
   Températureto warm up to RT
5. 5
   Extractionextracted with EtOAc
6. 6
   AutreThe combined organic extracts were evaporated
7. 7
   workup.DISSOLUTIONdissolved in ether (50 ml)
8. 8
   workup.ADDITIONtreated with conc. HCl (10 ml) for 30 min
9. 9
   Températureat reflux
10. 10
    Extractionextracted with EtOAc
11. 11
    SéchageThe combined organic extracts were dried over MgSO4
12. 12
    Autreevaporated

Mode opératoire

3-(Benzyloxy)cyclobutanone Methylsulfinyl(methylthio)methane (13 ml, 125 mmol) was dissolved in 250 ml THF and cooled to −20° C. n-Butyllithium (50 ml, 125 mmol) was added and the mixture was stirred for 3 h at −20° C. The mixture was cooled down to −78° C. and a solution of 1-((1,3-dibromopropan-2-yloxy)methyl)benzene (16.000 g, 52 mmol) was added. The reaction was stirred over night and allowed to warm up to RT. It was stirred for an additional 6h at RT, hydrolyzed with water and extracted with EtOAc. The combined organic extracts were evaporated, dissolved in ether (50 ml) and treated with conc. HCl (10 ml) for 30 min at reflux. The mixture was neutralized with NaOH (10M) and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and evaporated. Glass col. Chrom. (10-50% EtOAc in Hex) gave 3-(benzyloxy)cyclobutanone as a yellow oil.

Source