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

HRID 1172826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172826
[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

Komponenten

9

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b99a6ec23c2e45b0893015d613d683f8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834036B2

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