4-Fluoro-2-(3-furanyl)-6-methylphenol → 4-Fluoro-2-methyl-6-(tetrahydro-3-furanyl)phenol

HRID 63389Notes

Reaction equation

HRID 63389 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([C:10]2[CH:14]=[CH:13][O:12][CH:11]=2)[CH:3]=1>CO.[C].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)[C:5]([OH:9])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 1

HCID 900021994-Fluoro-2-(3-furanyl)-6-methylphenol2×

Product 1

HCID 900024614-Fluoro-2-methyl-6-(tetrahydro-3-furanyl)phenolYield 76.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-fluoro-2-(furan-3-yl)-6-methylphenol (Compound 6-11) (471 mg, 2.45 mmol) were dissolved in methanol. Palladium carbon (64.3 mg, 5 wt %) was added thereto, followed by stirring under hydrogen balloon for 24 hours. After the completion of the reaction, the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography (silica gel; hexane/ethyl acetate, 9/1) to obtain 4-fluoro-2-methyl-6-(tetrahydrofuran-3-yl)phenol (368 mg, 76%) as a white solid.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe concentrate was purified by column chromatography (silica gel; hexane/ethyl acetate, 9/1)

Sources & evidence

ORD record
ord-e773a31ef3d840e982973265efadae63
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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