反応 #79478

反応方程式

triethylamine

m-aminophenol

1,4-dibromobutane

→

3-pyrrolidinylphenol

収率 32.2%

溶媒

toluene

反応条件

後処理

1. 1
   その他triturated with diethylether
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   抽出extracted with 1M NaOH, water, and sat. NaCl
4. 4
   乾燥After drying the organic layer with MgSO4
5. 5
   ろ過filtering
6. 6
   その他evaporating solvent under vacuum
7. 7
   その他the crude product was purified by silica gel chromatography
8. 8
   その他to give a pale yellow solid
9. 9
   温度cooled to room temperature
10. 10
    洗浄washed with water and sat. NaCl
11. 11
    乾燥The solution was dried again over MgSO4
12. 12
    ろ過filtered
13. 13
    その他evaporated under vacuum

実験手順

A solution of m-aminophenol (12.6 gm, 0.115 moles) and 1,4-dibromobutane (50 gm, 0.23 moles) was heated to 130° C. for 12 hr. The mixture was cooled to room temperature and triturated with diethylether and then ethyl acetate. The residue was dissolved in ethyl acetate and extracted with 1M NaOH, water, and sat. NaCl. After drying the organic layer with MgSO4, filtering, and evaporating solvent under vacuum, the crude product was purified by silica gel chromatography to give a pale yellow solid. The solid was refluxed with 500 ml toluene and 17 ml triethylamine (0.12 moles) for one hr, cooled to room temperature and washed with water and sat. NaCl. The solution was dried again over MgSO4, filtered, and evaporated under vacuum to give 3-pyrrolidinylphenol as a white solid (6.0 gm, 0.037 moles, 32%).

出典