Tetrahydrofuran → 1-(4'-Trifluoromethyl-biphenyl-4-yl)-butan-2-one

HRID 1669288Notes

Reaction equation

HRID 1669288 reaction equation
[CH2:1]([Mg]Br)[CH3:2].O1CCCC1.CON(C)[C:13](=[O:31])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1>C(OCC)(=O)C.CCCCCC>[F:28][C:27]([F:29])([F:30])[C:24]1[CH:23]=[CH:22][C:21]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][C:13](=[O:31])[CH2:1][CH3:2])=[CH:16][CH:17]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 86085431N-Methoxy-N-methyl-2-(4'-trifluoromethyl-biphenyl-4-yl)-acetamideHCID 178418443HCID 178418443, compound

Product 1

HCID 673416551-(4'-Trifluoromethyl-biphenyl-4-yl)-butan-2-oneYield 42.9%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Ethyl magnesium bromide (1.15 mmol, 3.0M in ethyl ether) is added drop-wise to a tetrahydro-furan (3 mL) solution of N-methoxy-N-methyl-2-(4′-trifluoromethyl-biphenyl-4-yl)-acetamide (0.248 g, 0.77 mmol) at −45° C. and stirred for one hour. Gradually raise temperature to −20° C. and stirred for one hour. The reaction is quenched by saturated ammonium chloride solution (1 mL) at 0° C., extracted with ethyl acetate and washed with water and brine. Organics are dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel with 0-30% ethyl acetate/hexane gradient gives 0.095 g (0.33 mmol, 42%) of the title compound.

Workup

  1. stirringGradually raise temperature to −20° C. and stirred for one hour
  2. customThe reaction is quenched by saturated ammonium chloride solution (1 mL) at 0° C.
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialOrganics are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd0c19367d6348baa96a40aa5771f2d8
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

Loading…