Cesium carbonate → HCID 86648421, compound
Reaction equation
[C:1]1([C:7](=[N:9][OH:10])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][C:13]([C:15]1([CH3:26])[O:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][CH2:24]Cl)[CH2:17][O:16]1)=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:11][O:12][C:13]([C:15]1([CH3:26])[O:16][CH2:17][CH:18]([CH2:21][CH2:22][CH2:23][CH2:24][O:10][N:9]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH2:19][O:20]1)=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 1-Phenyl-ethanone oxime (1.13 g), Methyl-5-(4-chloro-butyl)-2-methyl-[1,3]dioxane-2-carboxylate (prepared by processes known) (2.5 g) and cesium carbonate (4.0 g) in anhydrous dimethyl formamide was stirred at 60° C. for 18 hours in an inert atmosphere. The reaction mixture was cooled to ambient temperature, poured into ice cold water and extracted with ethyl-acetate. The combined organic extract was washed with water, brine solution, dried over sodium sulphate and evaporated under reduced pressure. Crude product was flash chromatographed over silica gel using 7% ethyl acetate in petroleum ether as eluent to obtain 2.5 g of pure product.
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- additionpoured into ice cold water
- extractionextracted with ethyl-acetate
- extractionThe combined organic extract
- washwas washed with water, brine solution
- dry with materialdried over sodium sulphate
- customevaporated under reduced pressure
- customchromatographed over silica gel using 7% ethyl acetate in petroleum ether as eluent
Sources & evidence
- ORD record
- ord-900d6596381c4b7795dbe2ad68332417
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268867B2
Reaction notes
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