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

HRID 602944

Reaction equation

HRID 602944 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 86616050HCID 86616050, compound

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-7652509f60e14ea5a4223489e5ed07c7
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Linked notes

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