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

HRID 2353417Notes

Reaction equation

HRID 2353417 reaction equation
[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]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27831332,4,5-Trifluorophenylboronic acidHCID 866160507-(Methoxycarbonyl)-8-{[(trifluoromethyl)sulfonyl]oxy}-4-oxa-1-oxoniaspiro[4.5]dec-7-ene

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-4dfde6489bd4467c944d9292d3eba634
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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