Ammonium Chloride → HCID 49766391, compound
Reaction equation
[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O:7]CC)=O)[CH3:2].[CH3:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][Mg]Cl)=[CH:16][CH:15]=1.[Cl-].[NH4+]>C1COCC1>[CH2:11]([O:10][CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:7])[CH2:13][C:14]1[CH:22]=[CH:21][C:17]([CH3:18])=[CH:16][CH:15]=1)[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Under an argon atmosphere, to a solution of ethyl diethoxyacetate (1.80 mL, 10.1 mmol) in THF (20 mL) was added slowly a THF solution of (32) prepared above at −78° C. After stirring at −78° C. for an hour, to this was added 20% aqueous solution of ammonium chloride (10 mL) and the product was extracted with ethyl acetate (×3). The organic layer was sequentially washed with water (×1) and saturated brine (×1), and dried over anhydrous sodium sulfate. After filtration, the mixture was concentrated under reduced pressure and the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=9/1) to give 1,1-diethoxy-3-(4-methylphenyl)propan-2-one (33) as a colorless oily substance (1.96 g, 8.27 mmol, 82.4%).
Workup
- customprepared above at −78° C
- extractionthe product was extracted with ethyl acetate (×3)
- washThe organic layer was sequentially washed with water (×1) and saturated brine (×1)
- dry with materialdried over anhydrous sodium sulfate
- filtrationAfter filtration
- concentrationthe mixture was concentrated under reduced pressure
- customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=9/1)
Sources & evidence
- ORD record
- ord-38f3a93cb030418389501734d528e90a
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546568B2
Reaction notes
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