Allyl bromide → Methyl 3-(4-(allyloxy)phenyl)-3-(ethoxyimino)propanoate
Reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH3:2].[CH2:18](Br)[CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[CH2:20]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:5](=[N:4][O:3][CH2:1][CH3:2])[CH2:6][C:7]([O:9][CH3:10])=[O:8])=[CH:12][CH:13]=1)[CH:19]=[CH2:18]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of crude methyl 3-(ethoxyimino)-3-(4-hydroxyphenyl)propanoate obtained from Step A at 0° C. was added allyl bromide (0.65 mL) and potassium carbonate (781 mg) in DMF (5 mL), and the resulting suspension was stirred at 0° C. for 2 h. Ethyl acetate and water were added, the aqueous layer was extracted with ethyl acetate (×3), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to give the title compound as an oil. The crude product was used in Step C without purification. HPLC retention time: 1.88 min (method A). MS (ESI) (M+H)+ 278.14.
Workup
- extractionthe aqueous layer was extracted with ethyl acetate (×3)
- washthe combined organic layers were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-12e2caa0a57e4a988e30117271ef2af7
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678784B2
Reaction notes
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