Phosphorus oxychloride → 2,2-Dimethylpropionic acid 2-[(4-formyl-3-methoxyphenyl)methylamino]ethyl ester
Reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][NH:15][CH2:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:12][CH:13]=1.[C:25]([O-])(=[O:27])C.[Na+]>CN(C=O)C>[CH:25]([C:13]1[CH:12]=[CH:11][C:10]([CH2:14][NH:15][CH2:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])=[CH:9][C:8]=1[O:7][CH3:6])=[O:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
POCl3 (5.8 g, 37.7 mmol) was added to 20 ml of DMF in an ice bath. After 40 minutes, 2,2-dimethylpropionic acid 2-[(3-methoxyphenyl)methylamino]ethyl ester (10 g, 37.7 mmol) dissolved in DMF (10 ml) was added dropwise. After the mixture was stirred for 16 hours, an aqueous sodium acetate solution (20%, 100 ml) was added dropwise thereto and the oily matter was subjected to extraction with ethyl acetate. Washing was performed with a saturated aqueous NaHCO3 solution (100 ml) and then with a saturated saline solution (100 ml). After drying over Na2SO4 and concentration, the residue was purified by silica gel chromatography to give a light yellow crystal (yield: 8.7 g (78.9%)).
Workup
- additionwas added dropwise
- extractionthe oily matter was subjected to extraction with ethyl acetate
- washWashing
- dry with materialAfter drying over Na2SO4 and concentration
- customthe residue was purified by silica gel chromatography
- customto give a light yellow crystal (yield: 8.7 g (78.9%))
Sources & evidence
- ORD record
- ord-63a05b3cedd9469986ea23a62c2f33f0
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846955B2
Reaction notes
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