Sodium ethoxide → 5-(N-ethyl-N-(4-((E)-2-(furan-2-yl)vinyl)phenyl)amino)pentan-1-ol
Reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[O:7][CH:6]=[CH:5][CH:4]=1.[CH2:27]([N:29]([C:36]1[CH:41]=[CH:40][C:39]([CH:42]=O)=[CH:38][CH:37]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[CH3:28].[O-]CC.[Na+]>C(O)C>[CH2:27]([N:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[C:36]1[CH:37]=[CH:38][C:39](/[CH:42]=[CH:2]/[C:3]2[O:7][CH:6]=[CH:5][CH:4]=2)=[CH:40][CH:41]=1)[CH3:28]Participants
5
Conditions
- Temperature
- 85 °C
Procedure
In a 200 mL flask, 1A (18.47 g, 43.6 mmol) and N-ethyl-N-(4-formyl phenyl)-5-aminopentyl alcohol 1B (10.27 g, 43.6 mmol) were dissolved in anhydrous ethanol (115 mL) under Ar at RT. In a separate flask, sodium ethoxide (2.97 g, 43.6 mmol) was dissolved in anhydrous ethanol (51 mL). The ethanolic sodium ethoxide solution was added by addition funnel to the solution containing the starting reagents. The reaction mixture was then heated to 85° C. and stirred for 4 hours. The reaction mixture was evaporated and the product was extracted into dichloromethane against water. The crude product was purified on silica gel using 1:1 hexane:ethyl acetate. Product 2 was a red viscous liquid.
Workup
- additioncontaining the starting reagents
- customThe reaction mixture was evaporated
- extractionthe product was extracted into dichloromethane against water
- customThe crude product was purified on silica gel using 1:1 hexane
Sources & evidence
- ORD record
- ord-7932f77bf30249689757960a094c7639
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250121B2
Reaction notes
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