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N,N,N',N'-Tetramethylethylenediamine → 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde

HRID 1525753
ノート
印刷プレビュー

反応式

HRID 1525753 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:25].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:47][C:29]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CN(C)CCN(C)C>CN(C=O)C>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:29]=[O:47])=[C:3]([CH3:25])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

生成物 1

HCID 866585204-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde収率 15%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
100 °C

実験手順

A reaction autoclave was charged with 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (0.10 g, 0.22 mmol), palladium dichloride cyclooctadiene complex (1.6 mg, 2.5 mol-%), xanthphos (9.7 mg, 7.5 mol-%), N,N,N′,N′-tetramethylethylene diamine (19.3 mg, 0.75 equiv.) and DMF (2 mL) and purged with synthesis gas (carbon monoxide:hydrogen=1:1) to 5 bar. The reaction autoclave was heated to 100° C. for 16 h and then cooled to ambient temperature. After release of the pressure, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel to yield the title compound (13 mg, 15%).

後処理

  1. custompurged with synthesis gas (carbon monoxide:hydrogen=1:1) to 5 bar
  2. temperaturecooled to ambient temperature
  3. concentrationAfter release of the pressure, the reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-499d5e87306c4603a0b467113f159c37
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085541B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート