Methyl iodide → HCID 86599506, compound

HRID 855129Notes

Reaction equation

HRID 855129 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([O:21][C:22]([F:25])([F:24])[F:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2.IC.[C:28]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:28][O:1][C:2]1[CH:3]=[C:4]([O:21][C:22]([F:25])([F:23])[F:24])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:13])([F:14])[F:15])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86599504HCID 86599504, compound

Product 1

HCID 86599506HCID 86599506, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of ethyl 8-hydroxy-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 621w, Step 2 (165 mg, 0.442 mmole), iodomethane (82.8 uL, 1.33 mmole), KI (7.34 mg, 0.0442 mmole), K2CO3 (184 mg, 1.33 mmole) in anhydrous DMF (5.0 mL) was stirred at room temperature for 17 hrs. The mixture was then poured into brine (100 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give a tan solid. The crude product was purified by silica chromatography (0%-25% EtOAc in hexanes) to give an assumed quantitative yield of the product as an off-white crystalline solid: EIHRMS m/z 386.0593 (M+, C15H12F6O5, Calc'd 386.0589).

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a tan solid
  7. customThe crude product was purified by silica chromatography (0%-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4b9994518c0a4ea699ebca654d1bffa7
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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