Methyl iodide → HCID 58292860, compound

HRID 1798095Notes

Reaction equation

HRID 1798095 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([F:16])[C:7]1=2)[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[F:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:17][CH3:19])[CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58292615HCID 58292615, compound

Product 1

HCID 58292860HCID 58292860, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl-2-(4-fluoro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.25 g, 1.0 mmol) in DMF (5 mL) was added potassium carbonate (0.14 g, 1.0 mmol), followed by iodomethane (0.42 g, 3.0 mmol). The reaction mixture was stirred at room temperature overnight and quenched by addition of brine (20 mL). The resulting mixture was extracted with EtOAc (25 mL×2) and the combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/4) on silica gel to give the title compound as a white solid. (253 mg, Yield: 94%). MS (ESI) m/z=269 [M+H]+.

Workup

  1. customquenched by addition of brine (20 mL)
  2. extractionThe resulting mixture was extracted with EtOAc (25 mL×2)
  3. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (EtOAc/PE=1/4) on silica gel

Sources & evidence

ORD record
ord-38223cc4707d43bcb73ced681954ff31
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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