Hydrochloric Acid → HCID 11384598, compound

HRID 1869288Notes

Reaction equation

HRID 1869288 reaction equation
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[O:10][C:6]=2[C:5]([O:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[CH:4][CH:3]=1.[CH2:23]([N:25]([CH2:31][CH3:32])[C:26](=[O:30])/[CH:27]=[CH:28]/[CH3:29])[CH3:24].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([C:9]1[O:10][C:6]2[C:5]([O:14][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[CH:4][CH:3]=[C:2](/[C:28](/[CH3:29])=[CH:27]/[C:26]([N:25]([CH2:31][CH3:32])[CH2:23][CH3:24])=[O:30])[C:7]=2[CH:8]=1)(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80271Tri-o-tolylphosphineHCID 53544532-ButenaMide, N,N-diethyl-, (E)-HCID 113143551-[4-Bromo-7-(1-phenylethoxy)benzofuran-2-yl]ethanone2×

Product 1

HCID 11384598HCID 11384598, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
84 °C

Procedure

1-[4-Bromo-7-(1-phenylethoxy)benzofuran-2-yl]ethanone (compound 3) (1.0 g, 2.79 mmol) and (E)-N,N-diethyl-2-butenamide (0.47 g, 3.35 mmol) were dissolved in triethylamine (10 ml), and the inside of the system was replaced by nitrogen gas. Palladium acetate (0.031 g, 0.14 mmol) and tri-o-tolylphosphine (0.085 g, 0.28 mmol) were added and the mixture was stirred with heating at 78-90° C. for 16 hr. After confirmation of the completion of the reaction by TLC, 5% HCl aqueous solution was added and the mixture was extracted with ethyl acetate. The mixture was washed with saturated brine, dried over MgSO4, and the solvent was evaporated to give a brown oil. Purification by silica gel column chromatography (hexane:acetone=5:1) was performed to give (E)-3-[2-acetyl-7-(1-phenylethoxy)benzofuran-4-yl]-N,N-diethyl-2-butenamide (0.51 g, yield 43.6%) as a pale-yellow crystal.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe mixture was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated
  6. customto give a brown oil
  7. customPurification by silica gel column chromatography (hexane:acetone=5:1)

Sources & evidence

ORD record
ord-19e8944c48184a8eb325e2d9537b6e81
Source dataset
uspto-grants-2009_12
Patent number
US07638540B2

Reaction notes

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