Ammonium Chloride → HCID 57704163, compound
Reaction equation
[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O:7]CC)=O)[CH3:2].[C:13]1([CH:19]([Mg]Cl)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>C1COCC1>[CH2:11]([O:10][CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:7])[CH:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:20])[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 (92) prepared above at −78° C. After stirring at −78° C. for 3 hours, 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=19/1) to give 1,1-diethoxy-3-phenylbutan-2-one (93) as a colorless oily substance (330 mg, 1.37 mmol, 13.7%).
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=19/1)
Sources & evidence
- ORD record
- ord-e09d7ef195224544afac4a9bf1fe50ec
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546568B2
Reaction notes
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