Benzaldehyde → HCID 10086774, compound
Reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.C(N(CC)CC)C.[C:25]([O:28][CH2:29][C:30](Cl)=[O:31])(=[O:27])[CH3:26]>C(Cl)Cl.CCCCCC>[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([N:15]2[C@H:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@H:29]([O:28][C:25](=[O:27])[CH3:26])[C:30]2=[O:31])=[CH:13][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 962 mg (4.56 mmol) of the imine derived from benzaldehyde and p-methoxy aniline, and 0.85 mL (6.07 mmol) of triethylamine in 15 mL of CH2Cl2 at -20° C. was added dropwise a solution of 413 mg (3.04 mmol) of α-acetoxy acetyl chloride in 15 mL of CH2Cl2. The reaction mixture was allowed to warm to 25° C. over an 18 h period. The reaction mixture was then diluted with 100 mL of CH2Cl2 and the solution was extracted with 30 mL of 10% aqueous HC1. The organic layer was washed with 30 mL of water and 30 mL of saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated to provide a solid mass. The solid was titurated with 50 mL of hexane and the mixture was filtered. The remaining solid was recrystallized from ethyl acetate/hexane to give 645 mg (68%) of cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one as white crystals, m.p. 163° C.
Workup
- extractionthe solution was extracted with 30 mL of 10% aqueous HC1
- washThe organic layer was washed with 30 mL of water and 30 mL of saturated aqueous sodium bicarbonate
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customto provide a solid mass
- filtrationthe mixture was filtered
- customThe remaining solid was recrystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-cb889c05fce445b3b68d11a0328fc165
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05574156
Reaction notes
Loading…