反応 #48331

反応方程式

3-(Benzyloxy)cyclobutanone Methylsulfinyl(methylthio)methane

n-Butyllithium

water

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

→

3-(benzyloxy)cyclobutanone

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度The mixture was cooled down to −78° C.
3. 3
   workup.STIRRINGThe reaction was stirred over night
4. 4
   温度to warm up to RT
5. 5
   抽出extracted with EtOAc
6. 6
   その他The 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
   温度at reflux
10. 10
    抽出extracted with EtOAc
11. 11
    乾燥The combined organic extracts were dried over MgSO4
12. 12
    その他evaporated

実験手順

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.

出典