Ethyl Acetate → 2-(2-Nitro-5-phenoxy-benzyl)-hex-5-enenitrile
Reaction equation
[C:1]([C:3]([CH2:11][C:12]1[CH:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14][C:13]=1[N+:25]([O-:27])=[O:26])([CH2:7][CH2:8][CH:9]=[CH2:10])C(O)=O)#[N:2].CCCCCCC.C(OCC)(=O)C>CC(N(C)C)=O>[N+:25]([C:13]1[CH:14]=[CH:15][C:16]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:17][C:12]=1[CH2:11][CH:3]([CH2:7][CH2:8][CH:9]=[CH2:10])[C:1]#[N:2])([O-:27])=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a round bottom flask equipped with a stir bar, condenser, and a nitrogen inlet 2-cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid (4.0 g, 10.92 mmol) was added and dissolved in dimethylacetamide (10 mL). The solution was heated to 150° C. for 3 hours. The reaction mixture was allowed to room temperature, then the solvent was removed under reduced pressure. The resulting crude product was dissolved in ethyl acetate and washed 3 times with 1N HCl followed by one wash with saturated brine solution. The organic layer was separated and dried with anhydrous sodium sulfate and the solvent was removed to yield crude material. The crude material was subjected to flash chromatography (mobile phase 9:1 heptane:ethyl acetate) to yield a yellow oil.
Workup
- additionwas added
- customwas allowed to room temperature
- customthe solvent was removed under reduced pressure
- dissolutionThe resulting crude product was dissolved in ethyl acetate
- washwashed 3 times with 1N HCl
- washwash with saturated brine solution
- customThe organic layer was separated
- dry with materialdried with anhydrous sodium sulfate
- customthe solvent was removed
- customto yield crude material
- customto yield a yellow oil
Sources & evidence
- ORD record
- ord-16ec7119c7d44877915d0e90f8caae53
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776882B2
Reaction notes
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