Sodium methanolate methanol → HCID 66760811, compound

HRID 1850393Notes

Reaction equation

HRID 1850393 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[C:6]=2[C:5]([CH3:14])=[CH:4][C:3]=1[CH3:15].[CH3:16][O-:17].[Na+].CO>[Cu](Br)Br.O>[CH3:16][O:17][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[C:6]=2[C:5]([CH3:14])=[CH:4][C:3]=1[CH3:15]

Participants

5

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 66759626HCID 66759626, compound

Product 1

HCID 66760811HCID 66760811, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 962WaterSolvent

Procedure

A mixture of 7-bromo-2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one (2.90 g, 10.8 mmol) synthesized in Reference Example 67, copper bromide (1.86 g, 13.0 mmol) and 28% sodium methoxide/methanol solution (60 mL) was stirred under heated reflux for 15 hours. After cooled to room temperature, the reaction solution was poured into water and extracted using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 99:1 to 94:6) to give 1.18 g of the title compound (yield: 50%).

Workup

  1. temperatureunder heated
  2. temperaturereflux for 15 hours
  3. extractionextracted
  4. washThe extract was washed with saturated saline
  5. customdried
  6. customAfter that, the solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 99:1 to 94:6)

Sources & evidence

ORD record
ord-0940796c49cd40f9b9dc66a511fe8ec0
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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