Ethanol → HCID 59204834, compound

HRID 2241890Notes

Reaction equation

HRID 2241890 reaction equation
[Cl:1][C:2]1[C:19]([Cl:20])=[CH:18][C:17]([O:21]CC2C=CC=CC=2)=[CH:16][C:3]=1[O:4][C:5]1[C:13]2[CH2:12][C:11](C)(C)[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH2:29]([OH:31])[CH3:30]>[Pd]>[CH3:9][C:13]1([CH3:5])[O:31][C:29]2[C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:5][O:4][C:3]3[CH:16]=[C:17]([OH:21])[CH:18]=[C:19]([Cl:20])[C:2]=3[Cl:1])=[CH:8][CH:7]=[CH:6][C:30]=2[CH2:12]1

Participants

4

Reactant 2

HCID 702EthanolHCID 86623925HCID 86623925, compound

Product 1

HCID 59204834HCID 59204834, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 0.5 gram (0.001 mole) of 7-{4-[2,3-dichloro-5-(phenylmethoxy)phenoxy}-2,2-dimethyl-2,3-dihydrobenzo[b]furan and 0.1 gram (catalyst) of 10% palladium on carbon in 75 mL of ethanol was placed in a Parr hydrogenation bottle and hydrogenated using a Parr hydrogenation apparatus. Upon the theoretical uptake of hydrogen gas, the reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 100% methylene chloride, then 5% methanol in methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.17 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationUpon the theoretical uptake of hydrogen gas, the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure to a residue
  4. customThe residue was purified with column chromatography on silica gel using 100% methylene chloride
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8ce592780c54f44a9f05e027b3e74a0
Source dataset
uspto-grants-2010_03
Patent number
US07671055B2

Reaction notes

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