Hydrochloric Acid → HCID 86662734, compound

HRID 2091170Notes

Reaction equation

HRID 2091170 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13](N(OC)C)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydride2×HCID 86662735HCID 86662735, compound

Product 1

HCID 86662734HCID 86662734, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (40 mL) of 3-bromo-N,5-dimethoxy-N-methyl-1-benzofuran-2-carboxamide (4.00 g) synthesized above in tetrahydrofuran was added lithium aluminum hydride (241 mg) at 0° C., and the mixture was stirred for 1 hr. Lithium aluminum hydride (241 mg) was additionally added, and the mixture was stirred at 0° C. for 1 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title object compound (880 mg, 27%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hr
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-69547a21ae764ddc821dacf1ffa1f57c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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