Ammonium Chloride → HCID 66724770, compound

HRID 1037601Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O:7]CC)=O)[CH3:2].[Si:13]([O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[CH2:24][Mg]Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[Cl-].[NH4+]>C1COCC1>[Si:13]([O:20][C:21]1[CH:22]=[C:23]([CH2:24][C:5](=[O:7])[CH:4]([O:3][CH2:1][CH3:2])[O:10][CH2:11][CH3:12])[CH:27]=[CH:28][CH:29]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15]

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 of (103) prepared above at −78° C. After stirring at −78° C. for an hour, to this was added 20% aqueous solution of ammonium chloride (30 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=10/1) to give 3-[3-(tert-butyldimethylsilyloxy]phenyl]-1,1-diethoxypropan-2-one (104) as a colorless oily substance (1.90 g, 5.39 mmol, 53.9%).

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=10/1)

Sources & evidence

ORD record: ord-23e7cbe0f438466b8e704c377bfda455
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546568B2

Reaction notes

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