Acetic Acid → HCID 23138601, compound
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[CH2:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:10][CH2:11][CH:12]\1[OH:13].[C:33]([OH:36])(=[O:35])[CH3:34]>ClCCl>[C:33]([OH:36])(=[O:35])[CH3:34].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[CH2:8][NH:9][CH2:10][CH2:11][CH:12]\1[OH:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of (E)-3-[(furan-2-yl)methylidene]-1-(triphenylmethyl)piperidin-4-ol (3.70 g) in dichloromethane (75 ml) was added acetic acid (10 ml) under ice-cooling, and the resulting mixture was stirred at 60° C. for 3 hours. After stirring, acetic acid (10 ml) was added to the reaction mixture, and the resulting mixture was furthermore stirred at 60° C. for 1.5 hours. The reaction mixture was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of methanol and dichloromethane (1:19 to 1:9) as the eluent to afford the title compound (2.81 g, yield: quantitative) as a pale brown solid.
Workup
- temperaturecooling
- stirringAfter stirring
- stirringthe resulting mixture was furthermore stirred at 60° C. for 1.5 hours
- customThe reaction mixture was evaporated in vacuo
- customthe residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-0eef703320584e9ba97b8766e92608c4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829580B2
Reaction notes
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