Iodine → HCID 58934593, compound

HRID 855013Notes

Reaction equation

HRID 855013 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]([C:13]([F:16])([F:15])[F:14])[O:10]2)=[CH:5][CH:4]=1.II.[I:24](O)(=O)(=O)=O>C(O)C.O>[I:24][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[O:10][CH:9]([C:13]([F:14])([F:15])[F:16])[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:7]2

Participants

6

Reactant 3

HCID 807IodineHCID 65185Metaperiodic acidHCID 57438999HCID 57438999, compound

Product 1

HCID 58934593HCID 58934593, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8 g (26.5 mmol) of ethyl 7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 60 mL of ethanol was added 2.8 g (11.2 mmol) of iodine, followed by addition of a solution of 9.0 g (39.5 mmol) of periodic acid in 25 mL of water. The resulting solution was heated to 70° C. for five hrs. After cooling to room temperature, the volatiles were removed, the residue was dissolved in ethyl acetate, and the organic phase washed with saturated aqueous sodium sulfite and satr' brine. The resultant solution was dried over anhydrous magnesium sulfate and the volatiles were removed. The residue was purified by silica gel chromatography with hexane/ethyl acetate mixture to afford 9.8 g (70%) of a light yellow solid: 1H NMR (CDCl3/300 MHz) 7.62(s, 1H), 7.60(s, 1H), 6.49(s, 1H), 5.69(q, J=6.9 Hz, 1H), 4.30(m, 2H), 3.89(s, 3H), 1.34(t, J=7.2 Hz, 3H). MS (ESI+) 428.9(M+1, 100). HRMS (EI) m/z calcd for (C14H12F3O4) 427.9732, found 427.9741.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe volatiles were removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe organic phase washed with saturated aqueous sodium sulfite and satr' brine
  5. dry with materialThe resultant solution was dried over anhydrous magnesium sulfate
  6. customthe volatiles were removed
  7. customThe residue was purified by silica gel chromatography with hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-49277182ca37457f991c39dbde00f587
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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