HCID 57810545, compound → HCID 57810593, compound

HRID 2106443Notes

Reaction equation

HRID 2106443 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:12]2[CH:13]=[C:14]([C:16]([C:21]3[CH:34]=[CH:33][C:24]([O:25][CH2:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[C:23]([CH3:35])[CH:22]=3)([CH2:19][CH3:20])[CH2:17][CH3:18])[O:15][C:11]=2[CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.CO.[Pd]>[CH2:17]([C:16]([C:21]1[CH:34]=[CH:33][C:24]([O:25][CH2:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:31])[CH3:30])=[C:23]([CH3:35])[CH:22]=1)([C:14]1[O:15][C:11]2[CH:10]=[C:9]([OH:8])[CH:37]=[CH:36][C:12]=2[CH:13]=1)[CH2:19][CH3:20])[CH3:18]

Participants

5

Reactant 1

HCID 57810545HCID 57810545, compound

Product 1

HCID 57810593HCID 57810593, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{4-[1-(6-benzyloxy-benzofuran-2-yl)-1-ethyl-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (5.90 g, 11.8 mmol) in EtOAc (20.0 mL) is added a slurry of Pd—C (590 mg, 10%) in MeOH (20.0 mL) at RT. The resulting mixture is stirred under hydrogen balloon pressure for 2 h. The mixture is filtered through a pad of celite and the filtrate is concentrated, the residue is purified with 20-30% EtOAc/Hex to afford the title compound (4.35 g, 90%).

Workup

  1. filtrationThe mixture is filtered through a pad of celite
  2. concentrationthe filtrate is concentrated
  3. customthe residue is purified with 20-30% EtOAc/Hex

Sources & evidence

ORD record
ord-d31c1808b4984bcc9cffd5b72690d597
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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