Methyl morpholine oxide → [4-(4-Chlorophenoxy)-2-propylphenyl][4-chloro-2-fluoro-5-methoxyphenyl]methanone

HRID 1172826ノート

反応式

HRID 1172826 の反応式
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[CH:14][C:13]=2[CH2:26][CH2:27][CH3:28])[OH:11])=[C:4]([F:29])[C:3]=1[Si](C)(C)C.C[N+]1([O-])CCOCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.C(OCC)C.C1COCC1.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:10]([C:5]3[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=3[F:29])=[O:11])=[C:13]([CH2:26][CH2:27][CH3:28])[CH:14]=2)=[CH:24][CH:23]=1

参加物

9

反応物 3

HCID 82029Methyl morpholine oxideHCID 2724141Tetrabutylammonium FluorideHCID 86622409[4-Chloro-2-fluoro-5-methoxy-3-(trimethylsilyl)phenyl][4-(4-chlorophenoxy)-2-propylphenyl]methanol

生成物 1

HCID 68689947[4-(4-Chlorophenoxy)-2-propylphenyl][4-chloro-2-fluoro-5-methoxyphenyl]methanone

試薬・触媒・溶媒 5

HCID 178419074HCID 178419074、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A mixture of the product from Step 2 (1.9 g, 3.7 mmol), N-methylmorpholine-N-oxide (0.70 g, 6.0 mmol), tetrapropylammonium perruthenate (70 mg, 0.2 mmol) and 4 Å molecular sieves (2.0 g) in dichloromethane (20 mL) was stirred at 25° C. for 1 h. The reaction mixture was diluted with diethyl ether (60 mL) and filtered through a short path of silica gel. Removal of the solvent gave the crude product. The crude product was dissolved in THF (20 mL) and treated with tetrabutylammonium fluoride (1M in THF, 5.6 mL, 5.6 mmol) for 10 min. The reaction mixture was diluted with ethyl acetate, washed with brine, dried and concentrated. The residue was purified by chromatography on silica gel to give the title product.

後処理

  1. filtrationfiltered through a short path of silica gel
  2. customRemoval of the solvent
  3. customgave the crude product
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-b99a6ec23c2e45b0893015d613d683f8
出典データセット
uspto-grants-2010_11
特許番号
US07834036B2

反応ノート

読み込み中…