Benzyloxyacetyl chloride → 1-(2-benzyloxyacetyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

HRID 68173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68173
[CH2:1]([O:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si]([O:20][C:21]1[C:30]2[C:25](=[C:26]([O:32][CH2:33][CH2:34][CH3:35])[CH:27]=[CH:28][C:29]=2[F:31])[N:24]=[CH:23][C:22]=1[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)(C(C)(C)C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][CH2:9][C:10]([N:24]1[C:25]2[C:30](=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH3:35])[C:21](=[O:20])[C:22]([C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)=[CH:23]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 674170464-(Tert-butyldimethylsilyloxy)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-quinolin

Produkt 1

HCID 584923631-(2-benzyloxyacetyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-oneAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzyloxyacetyl chloride (1.9 ml, 3 equivalent weight) was added to a dichloromethane solution (50 ml) of 4-(tert-butyldimethylsilyloxy)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-quinolin (1.5 g, 3.4 mmol) while ice-cooling and the mixture was stirred overnight at room temperature. An aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction using ethyl acetate. The thus-obtained organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=2:1). The purified product was concentrated under reduced pressure, giving a colorless oily substance of 1-(2-benzyloxyacetyl)-5-fluoro -3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (250 mg, yield: 15%).

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction
  3. dry with materialThe thus-obtained organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified
  6. concentrationThe purified product was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-72e64c8d365e48549dc92681a5cbe5fa
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045108E1

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