Hydrochloric Acid → HCID 66760629, compound

HRID 1850398Notes

Reaction equation

HRID 1850398 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]([CH3:11])[CH2:7][C:6]=2[C:5]([CH3:12])=[CH:4][C:3]=1[CH3:13].C[O-].[Na+].CO.CN([CH:22]=[O:23])C.Cl>C(OCC)(=O)C.[Cu](I)I>[CH3:22][O:23][C:2]1[C:10]2[O:9][CH:8]([CH3:11])[CH2:7][C:6]=2[C:5]([CH3:12])=[CH:4][C:3]=1[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 23694274Sodium methanolate methanolHCID 66759624HCID 66759624, compound

Product 1

HCID 66760629HCID 66760629, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-bromo-2,4,6-trimethyl-2,3-dihydro-1-benzofuran (10.0 g, 41.5 mmol) synthesized in Reference Example 79, copper iodide (I) (7.88 g, 41.5 mmol), 28% sodium methoxide/methanol solution (41.5 mL) and DMF (20.7 mL) was stirred at 120° C. for 2 hours. After cooled, 3N hydrochloric acid was added to the reaction solution to be neutralized, and it was diluted with ethyl acetate. Insolubles were removed by Celite filtration, and the obtained filtrate was washed with water and saturated saline. The organic layer was dried using magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 94:6) to give 5.5 g of the title compound as an oily product (yield: 69%).

Workup

  1. temperatureAfter cooled
  2. customInsolubles were removed by Celite filtration
  3. washthe obtained filtrate was washed with water and saturated saline
  4. customThe organic layer was dried
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 94:6)

Sources & evidence

ORD record
ord-eed2878a3eb8479c896217542cebcf75
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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