HCID 22630267, compound → HCID 22630264, compound

HRID 2416356Notes

Reaction equation

HRID 2416356 reaction equation
[CH2:1]([O:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([C:20]#[C:21][C:22]4[CH:27]=[CH:26][C:25]([O:28]CC5C=CC=CC=5)=[C:24]([F:36])[CH:23]=4)=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]>[Pd].O1CCCC1>[CH2:1]([O:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([F:36])[CH:23]=4)=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 22630267HCID 22630267, compound

Product 1

HCID 22630264HCID 22630264, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Pentyloxy-7-[2-(3-fluoro-4-benzyloxyphenyl)ethynyl]fluorene (1 g) and palladium on carbon (0.02 g) were stirred in tetrahydrofuran (30 mL) at an atmospheric pressure under hydrogen atmosphere. Absorption of hydrogen was stopped after 2 hours, and therefore the reaction mixture was filtered to remove the catalyst, followed by distilling the solvent off. The residue was recrystallized twice from acetone to obtain 2-pentyloxy-7-(2-(3-fluoro-4-hydroxyphenyl)ethyl)fluorene (0.7 g) of colorless needle crystal.

Workup

  1. customAbsorption of hydrogen
  2. filtrationthe reaction mixture was filtered
  3. customto remove the catalyst
  4. distillationby distilling the solvent off
  5. customThe residue was recrystallized twice from acetone

Sources & evidence

ORD record
ord-6e29847868fd499aa1b172a4b5301ca5
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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