Ammonium Chloride → HCID 66724860, compound

HRID 1748895Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O:7]CC)=O)[CH3:2].[CH2:13]([C:15]1[CH:23]=[CH:22][C:18]([CH2:19][Mg]Cl)=[CH:17][CH:16]=1)[CH3:14].[Cl-].[NH4+]>C1COCC1>[CH2:11]([O:10][CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:7])[CH2:19][C:18]1[CH:22]=[CH:23][C:15]([CH2:13][CH3:14])=[CH:16][CH:17]=1)[CH3:12]

Participants

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 (42) of (4-ethylbenzyl)magnesium chloride 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-ethylphenyl)propan-2-one (43) as a colorless oily substance (1.29 g, 5.04 mmol, 50.6%).

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-4a026dfbd1df497eb65f6d44fe855ada
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09151739B2

Reaction notes

Loading…