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

HRID 386749ノート

反応式

HRID 386749 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-85d74b786e114ceb973fa16d3903a4ef
出典データセット
uspto-grants-2013_02
特許番号
US08372867B2

反応ノート

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