Sodium Hydroxide → 8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 602936

Reaktionsgleichung

Reaktionsgleichung von HRID 602936
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[C:22]1(O)[CH2:31][CH2:30][C:25]2([O:29][CH2:28][CH2:27][O:26]2)[CH2:24][CH2:23]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[C:22]1[CH2:31][CH2:30][C:25]2([O:26][CH2:27][CH2:28][O:29]2)[CH2:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrate2×HCID 574243598-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Produkt 1

HCID 574243608-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a round-bottomed flask (3 L) under nitrogen atmosphere equipped with a Dean-Stark trap, toluene (350 mL), para-toluenesulfonic acid monohydrate (p-TSA) (1 g) and 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (94.2 g) were added and the mixture was refluxed overnight. Additional p-TSA (1 g) was added. Refluxing was continued overnight and then the reaction was stirred at room temperature for two more days. The reaction mixture was treated with 0.1N aqueous sodium hydroxide solution (500 mL) and extracted with heptanes (500 mL). The organic layer was washed with water (3×500 mL), dried over anhydrous sodium sulfate, filtered and evaporated to yield crude product which was purified by column chromatography (silica gel, gradient 2% to 40% ethyl acetate in heptanes) to yield the title compound.

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was refluxed overnight
  3. temperatureRefluxing
  4. extractionextracted with heptanes (500 mL)
  5. washThe organic layer was washed with water (3×500 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto yield crude product which
  10. customwas purified by column chromatography (silica gel, gradient 2% to 40% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-0539040d7efb454d88ce51c2d91a8281
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906649B2

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