Ethanol → 1,1-Diethoxy-3-[4-(trifluoromethyl)phenyl]propan-2-one

HRID 1748899Notes

Reaction equation

HRID 1748899 reaction equation
[N+](=[CH:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[N-].Cl[O:18][C:19]([CH3:22])(C)C.[CH2:23]([OH:25])[CH3:24]>>[CH2:23]([O:25][CH:3]([O:18][CH2:19][CH3:22])[C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 521297Tert-Butyl hypochloriteHCID 76661292HCID 76661292, compound

Product 1

HCID 667246491,1-Diethoxy-3-[4-(trifluoromethyl)phenyl]propan-2-one

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 1-diazo-3-[4-(trifluoromethyl)phenyl]propan-2-one (53) (661 mg, 2.90 mmol) was dissolved in anhydrous ethanol (6 mL) and cooled to 0° C. To this was added tert-butyl hypochlorite (330 μL, 2.92 mmol) and stirred for an hour at the same temperature. After being concentrated under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=18/1) to give 1,1-diethoxy-3-[4-(trifluoromethyl)phenyl]propan-2-one (54) as a colorless oily substance (544 mg, 1.87 mmol, 64.7%).

Workup

  1. concentrationAfter being concentrated under reduced pressure
  2. customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=18/1)

Sources & evidence

ORD record
ord-386872e8e56a47c2a3e0e98743143908
Source dataset
uspto-grants-2015_10
Patent number
US09151739B2

Reaction notes

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