反応 #69073

反応方程式

acetic acid

4-aminobutanol

3-benzoyloxybenzenesulfonyl chloride

DBU

→

title compound

3-(cyclopropylmethoxy)-N-(4-(methoxymethoxy)butyl)benzenesulfonamide

溶媒

methanol

反応条件

後処理

1. 1
   その他obtained
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 10 minutes
3. 3
   濃縮The reaction mixture was then concentrated under reduced pressure
4. 4
   その他The residue was purified by silica gel column chromatography (100% ethyl acetate)
5. 5
   workup.DISSOLUTIONThe obtained colorless oil (147 mg) was dissolved in DMF (4.0 mL)
6. 6
   workup.ADDITIONTo the solution, potassium carbonate (141 mg), potassium iodide (8.5 mg), and (chloromethyl)cyclopropane (47 μL) were added
7. 7
   workup.STIRRINGthe mixture was stirred at 90° C. for 14 hours
8. 8
   温度The reaction mixture was cooled to room temperature
9. 9
   workup.ADDITIONwater (10 mL) was then added
10. 10
    抽出the resultant mixture was then extracted with ethyl acetate (10 mL)
11. 11
    洗浄The organic layer was washed with water (10 mL) and brine (10 mL)
12. 12
    乾燥dried over anhydrous sodium sulfate
13. 13
    濃縮concentrated under reduced pressure
14. 14
    その他The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

実験手順

A colorless oil (285 mg) was obtained according to the method of Reference Example 233 from 4-aminobutanol (89 mg) and 3-benzoyloxybenzenesulfonyl chloride (300 mg) obtained according to a method described in the document (J. Pesticide. Chem., 13, 107-115 (1988)). This oil was dissolved in methanol (5.0 mL). To the solution, DBU (441 mg) was added, and the mixture was stirred at room temperature for 45 minutes. To the reaction mixture, acetic acid (210 μL) was added, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100% ethyl acetate). The obtained colorless oil (147 mg) was dissolved in DMF (4.0 mL). To the solution, potassium carbonate (141 mg), potassium iodide (8.5 mg), and (chloromethyl)cyclopropane (47 μL) were added, and the mixture was stirred at 90° C. for 14 hours. The reaction mixture was cooled to room temperature, water (10 mL) was then added thereto, and the resultant mixture was then extracted with ethyl acetate (10 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain the title compound (91 mg) as a colorless oil.

出典