Triphenylphosphine → 3-(4-Methylphenyl)-5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydroisoxazole

HRID 386749Notes

Reaction equation

HRID 386749 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3](O)([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=[N:6][OH:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OC)(C)(C)C>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH2:4][C:3]([C:2]([F:26])([F:27])[F:1])([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:16]=3)[O:7][N:6]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 866433804,4,4-Trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one oxime

Product 1

HCID 866433813-(4-Methylphenyl)-5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydroisoxazoleYield 25.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 4,4,4-trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one oxime (0.45 g) and triphenylphosphine (0.60 g) in tetrahydrofuran (10 mL), diethyl azodicarboxilate (0.44 g) was added, and the mixture was stirred for 24 hours at room temperature. After the reaction solution was diluted with t-butylmethylether, the solution was washed with water and saturated brine and the organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to yield 3-(4-methylphenyl)-5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydroisoxazole (0.11 g).

Workup

  1. washthe solution was washed with water and saturated brine
  2. dry with materialthe organic layer was then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-85d74b786e114ceb973fa16d3903a4ef
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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