Sodium methanolate methanol → HCID 90384391, compound

HRID 928680Notes

Reaction equation

HRID 928680 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8]([CH2:11]Br)=[CH:7][C:6]=2[C:5]([F:13])=[C:4]([F:14])[CH:3]=1.[CH3:15][OH:16].C[O-].[Na+]>CO>[Br:1][C:2]1[C:10]2[O:9][C:8]([CH2:11][O:16][CH3:15])=[CH:7][C:6]=2[C:5]([F:13])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 90384352HCID 90384352, compound

Product 1

HCID 90384391HCID 90384391, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (489 mg, 1.50 mmol) of Step 1 of Example 54 was dissolved in methanol (7 mL), and a 25% sodium methoxide methanol solution (1.5 mL) were added thereto, and heated under reflux for 3 hours. The resultant was returned to room temperature, and the solvent was distilled away under reduced pressure. The resulting residue was diluted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane/ethyl acetate) to thus obtain the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customwas returned to room temperature
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionThe resulting residue was diluted with ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled away under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d6093fb1581541f195bdd9c586711cec
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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