HCID 69685147, compound → HCID 69685014, compound

HRID 2085600Notes

Reaction equation

HRID 2085600 reaction equation
[CH2:1]([O:3][C:4](=[O:19])/[CH:5]=[CH:6]/[C:7]1[C:15]2[O:14][CH2:13][C:12]([CH3:17])([CH3:16])[C:11]=2[CH:10]=[C:9](Br)[CH:8]=1)[CH3:2]>C(OCC)(=O)C.[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[C:15]2[O:14][CH2:13][C:12]([CH3:17])([CH3:16])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 1

HCID 69685147HCID 69685147, compound2×

Product 1

HCID 69685014HCID 69685014, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-3-(5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-acrylic acid ethyl ester (Intermediate 74, 0.97 g, 2.98 mmol) in 13 mL of ethyl acetate was treated with a slurry of 10% palladium on carbon (0.25 g) in 7 mL of ethanol and the resulting reaction mixture was stirred overnight under an atmosphere of hydrogen. The solids were then filtered over a bed of celite and the filtrate was evaporated to an oil. The oil was dissolved in dichloromethane and washed with water. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound as a pale yellow oil (0.71 g, 96%).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe solids were then filtered over a bed of celite
  3. customthe filtrate was evaporated to an oil
  4. dissolutionThe oil was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a0af0c4f5f104b549790afe7c73db698
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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