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

HRID 1616970Notes

Reaction equation

HRID 1616970 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-ad3de7f012654f948ad848ce43a91ed2
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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