Sodium Chlorite → HCID 69517888, compound

HRID 854959Notes

Reaction equation

HRID 854959 reaction equation
[CH3:1][C:2]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]([C:16]([F:19])([F:18])[F:17])[O:13]2)=[CH:8][CH:7]=1)([CH3:5])[CH:3]=[O:4].[O-:25]Cl=O.[Na+]>O1CCOCC1.O>[CH2:23]([O:22][C:20]([C:11]1[CH:12]([C:16]([F:19])([F:17])[F:18])[O:13][C:14]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([C:2]([CH3:1])([CH3:5])[C:3]([OH:25])=[O:4])[CH:15]=2)=[O:21])[CH3:24]

Participants

5

Reactant 2

HCID 23668197Sodium ChloriteHCID 86599474HCID 86599474, compound

Product 1

HCID 69517888HCID 69517888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 7-(1,1-dimethyl-2-oxoethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate (500 mg, 1.46 mmoles) in 20 mL of dioxane was added a solution of 80% NaClO2 (727 mg, (582 mg), 6.43 mmoles) in 5 mL of water. The resulting mixture was stirred in an oil bath at 90° C. for 1.5 h, and cooled. The mixture was partitioned between DCM and water, further extracted, and the combined organic extracts dried over Na2SO4, filtered, and evaporated. Chromatography of the residue over silica gel using 30% EtOAc—hexane—1% HOAc as eluent gave the title compound, 400 mg, as an oil.

Workup

  1. temperaturecooled
  2. customThe mixture was partitioned between DCM and water
  3. extractionfurther extracted
  4. dry with materialthe combined organic extracts dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0a459a880dcb441f86d95300a2717d1f
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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