Water → HCID 58288389, compound

HRID 1476137Notes

Reaction equation

HRID 1476137 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.F[B-](F)(F)F.[O:22]=[N+:23]=[O:24].O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:15])([CH3:16])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:7]=1[N+:23]([O-:24])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 11073463Nitronium tetrafluoroborateHCID 58288282HCID 58288282, compound

Product 1

HCID 58288389HCID 58288389, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

276 mg (1.45 mmol) of ethyl 3-(4-chlorophenyl)-3-methylbutanoate were dissolved in 10 ml of dichloromethane, and the mixture was cooled to 0° C. A little at a time, 278 mg (1.38 mmol) of nitronium tetrafluoroborate were then added, and the mixture was stirred at a temperature between 0° C. and 10° C. for 4 h. 10 ml of water and 10 ml of dichloromethane were then added, and the phases were separated. The organic phase was dried over magnesium sulphate and concentrated to dryness. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 223 mg of the title compound (68% of theory).

Workup

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-1bc8508b54634138bae7809f3cccf449
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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