N-Methoxy-N-methyl-4-(5-trifluoromethyl-isoxazol-3-yl)-benzamide → 2,2-Dimethyl-1-[4-(5-trifluoromethyl-isoxazol-3-yl)-phenyl]-propan-1-one

HRID 1409797Notes

Reaction equation

HRID 1409797 reaction equation
CON(C)[C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)=[CH:7][CH:6]=1.[C:22]([Mg]Br)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[CH3:23][C:22]([CH3:25])([CH3:24])[C:4]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[O:13][N:12]=2)=[CH:9][CH:10]=1)=[O:20]

Participants

4

Reactant 2

HCID 57606119N-Methoxy-N-methyl-4-(5-trifluoromethyl-isoxazol-3-yl)-benzamideHCID 178418586HCID 178418586, compound

Product 1

HCID 576061032,2-Dimethyl-1-[4-(5-trifluoromethyl-isoxazol-3-yl)-phenyl]-propan-1-oneYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared from N-Methoxy-N-methyl-4-(5-trifluoromethyl-isoxazol-3-yl)-benzamide and a 1.7 N THF solution of tert-butylmagnesium bromide as described in Example 5. Chromatographed on silica gel with EtOAc/hexanes (5 then 10%) as eluant to afford product as a colorless solid (21 mg, 7%). 1H NMR (CDCl3) 1.37 (s, 9 H), 7.05 (s, 1 H), 7.79 (d, J=8.4, 2 H), 7.87 (d, J=7.9, 2 H). 19F NMR −64.6. LC/MS 7.28 min, [M+1]+298.

Workup

  1. customChromatographed on silica gel with EtOAc/hexanes (5

Sources & evidence

ORD record
ord-5ed52ae0b1de4e0ba78d56f0836a0106
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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