反応 #652465

反応方程式

K2CO3

(4-methoxy-benzenesulfonyl)-acetic acid ethyl ester

benzyl bromide

18-Crown-6

→

2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester

溶媒

acetone

反応条件

後処理

1. 1
   温度the mixture was refluxed for 24 hours
2. 2
   ろ過At the end, the reaction mixture was filtered
3. 3
   濃縮the acetone layer was concentrated
4. 4
   その他The residue obtained
5. 5
   抽出was extracted with chloroform
6. 6
   洗浄washed well with water
7. 7
   乾燥dried over anhydrous MgSO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated
10. 10
    その他The product obtained
11. 11
    その他was purified by silica-gel column chromatography
12. 12
    洗浄eluting with 30% ethyl acetate

実験手順

To stirred solution of the (4-methoxy-benzenesulfonyl)-acetic acid ethyl ester (2.5 g, 10 mmol), benzyl bromide (1.8 gm, 10 mmol) and 18-Crown-6 (500 mg) in acetone (250 ml) was added K2CO3 (10 gms, excess) and the mixture was refluxed for 24 hours. At the end, the reaction mixture was filtered and the acetone layer was concentrated. The residue obtained was extracted with chloroform, washed well with water, dried over anhydrous MgSO4, filtered and concentrated. The product obtained was purified by silica-gel column chromatography, eluting with 30% ethyl acetate: hexane. The product, 2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester was isolated as a low melting solid. Yield: 3.0 gm 86%; Low melting solid; MS: 349 (M+H)+.

出典