Sodium Carbonate → Methyl 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene-7-carboxylate

HRID 1454788

Reaktionsgleichung

Reaktionsgleichung von HRID 1454788
[CH3:1][O:2][C:3]([C:5]1[CH2:6][C:7]2([CH2:12][CH2:13][C:14]=1OS(C(F)(F)F)(=O)=O)[OH+:11][CH2:10][CH2:9][O:8]2)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[F:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1B(O)O>CN(C)C=O>[F:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1[C:14]1[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27831332,4,5-Trifluorophenylboronic acidHCID 86616050HCID 86616050, Verbindung

Produkt 1

HCID 67065857Methyl 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 7-(methoxycarbonyl)-8-{[(trifluoromethyl)sulfonyl]oxy}-4-oxa-1-oxoniaspiro[4.5]dec-7-ene (5.65 g, 16.0 mmol) dissolved in N,N-dimethylformamide (190 mL) were added aqueous sodium carbonate solution (2.0M, 20 mL, 39.0 mmol) and 2,4,5-trifluorophenylboronic acid (4.11 g, 23.4 mmol). The resulting mixture was degassed and treated with PdCl2(dppf) ([1,1′-bis(diphenylphosphino)-ferrocene] dichloropalladium(II), complex with dichloromethane (1:1), 1274 mg). The resulting mixture was stirred under a nitrogen atmosphere at room temperature overnight, filtered over Celite, diluted with ethyl acetate and washed with water. The organic phase was dried over anhydrous sodium sulfate, evaporated and the crude product was purified by chromatography on a Biotage® system (silica gel, ethyl acetate in hexanes gradient 30-50%) to yield the title compound.

Aufarbeitung

  1. customThe resulting mixture was degassed
  2. additiontreated with PdCl2(dppf) ([1,1′-bis(diphenylphosphino)-ferrocene] dichloropalladium(II), complex with dichloromethane (1:1), 1274 mg)
  3. filtrationfiltered over Celite
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customevaporated
  8. customthe crude product was purified by chromatography on a Biotage® system (silica gel, ethyl acetate in hexanes gradient 30-50%)

Quellen und Nachweise

ORD-Eintrag
ord-99eed27c1b4c4d5691915f07a75158f2
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482336B2

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