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

HRID 2264282

Reaction equation

HRID 2264282 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round-bottomed flask (3 L) under nitrogen atmosphere equipped with a Dean-Stark trap, toluene (350 mL), para-toluenesulphonic 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.

Workup

  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)

Sources & evidence

ORD record
ord-9b65e534079a43139462f7c8dd8298b6
Source dataset
uspto-grants-2010_12
Patent number
US07855206B2

Linked notes

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