反应 #48331

反应方程式

3-(Benzyloxy)cyclobutanone Methylsulfinyl(methylthio)methane

n-Butyllithium

water

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

→

3-(benzyloxy)cyclobutanone

溶剂

THF

反应条件

后处理

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
   萃取extracted with EtOAc
6. 6
   其他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
    萃取extracted with EtOAc
11. 11
    干燥The combined organic extracts were dried over MgSO4
12. 12
    其他evaporated

实验过程

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.

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