HCID 86623857, compound → HCID 86623858, compound

HRID 1919529Notes

Reaction equation

HRID 1919529 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:8]=[CH:9][CH:10]2[O:15][CH2:14][CH2:13][O:12][CH2:11]2)[CH:7]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH2:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][O:12][CH2:11]2)[CH:7]=1

Participants

4

Reactant 1

HCID 86623857HCID 86623857, compound

Product 1

HCID 86623858HCID 86623858, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution 7 (1.75 g, 7.3 mmol) in ethanol (200 proof, 80 mL) under Ar was added Pd/C (10%, 300 mg). The flask containing the mixture was evacuated to the point of boiling and purged with H2 three times. Then a H2 balloon was attached to the flask and the reaction was stirred for 72 h at room temperature. The reaction mixture was then filtered through a pad of Celite eluted with EtOH. The crude product was obtained by removal of the solvent in vacuo. 1H NMR (CDCl3, 500 MHz): δ 6.87-6.72 (m, 3 H), 4.87 (t, J=3.8 Hz, 1 H), 3.97-3.95 (m, 2 H), 3.86-3.83 (m, 2 H), 3.79 (s, 3 H), 2.64-2.62 (m, 2 H), 2.44 (td, J=1.7, 7.2 Hz, 2 H), 1.92 (quintet, J=7.5 Hz, 2 H).

Workup

  1. additionThe flask containing the mixture
  2. customwas evacuated to the point
  3. custompurged with H2 three times
  4. filtrationThe reaction mixture was then filtered through a pad of Celite
  5. washeluted with EtOH

Sources & evidence

ORD record
ord-0bec439901fc4e769cd14bc142f707c1
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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