反応 #69072

反応方程式

4-Aminobutanol

THF

magnesium oxide

water

benzenesulfonyl chloride

→

title compound

N-(4-(methoxymethoxy)butyl)benzenesulfonamide

反応条件

後処理

1. 1
   その他The precipitate was removed by filtration
2. 2
   洗浄washed with chloroform (50 mL)
3. 3
   濃縮Then, the combined filtrate was concentrated under reduced pressure
4. 4
   workup.ADDITIONTo the residue, water (20 mL) was added
5. 5
   抽出the resultant mixture was then extracted with ethyl acetate (20 mL)
6. 6
   洗浄The organic layer was washed with brine (20 mL)
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The residue was purified by silica gel column chromatography (100% ethyl acetate)
10. 10
    workup.DISSOLUTIONThe obtained colorless oil (1.48 g) was dissolved in dichloromethane (7.5 mL)
11. 11
    workup.ADDITIONTo the solution, N,N-diisopropylethylamine (3.43 mL) and chloromethyl methyl ether (1.0 mL) were added
12. 12
    workup.STIRRINGthe mixture was stirred at room temperature for 1.5 hours
13. 13
    濃縮The reaction mixture was concentrated under reduced pressure
14. 14
    その他the residue was then purified by silica gel column chromatography (50% ethyl acetate/hexane)

実験手順

4-Aminobutanol (700 mg) was dissolved in THF (12.5 mL). To the solution, magnesium oxide (1.58 g), water (3.2 mL), and benzenesulfonyl chloride (1.15 mL) were added, and the mixture was stirred at room temperature for 2 hours. The precipitate was removed by filtration, and washed with chloroform (50 mL). Then, the combined filtrate was concentrated under reduced pressure. To the residue, water (20 mL) was added, and the resultant mixture was then extracted with ethyl acetate (20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100% ethyl acetate). The obtained colorless oil (1.48 g) was dissolved in dichloromethane (7.5 mL). To the solution, N,N-diisopropylethylamine (3.43 mL) and chloromethyl methyl ether (1.0 mL) were added, and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (50% ethyl acetate/hexane) to obtain the title compound (1.36 g) as a colorless oil.

出典