5-(4-Methoxyphenyl)pent-4-yn-1-ol → HCID 12862955, compound

HRID 25101Notes

Reaction equation

HRID 25101 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:5][CH:4]=1.[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 115501385-(4-Methoxyphenyl)pent-4-yn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 12862955HCID 12862955, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 16 (7.1 g, 37 mmol) in 150 dry ethanol (150 mL) was placed in a 0.5 L Parr flask and palladium on carbon (0.92 g, 5% wet. Pd/C) was added as a suspension in ethanol (25 mL). The reaction mixture was shaken at 50 psi of hydrogen pressure at room temperature for 24 hours. After this time, the mixture was filtered through a silica gel pad and the solvent was removed at reduced pressure. The residue was purified by flash chromatography (silica gel, 1:3 ethyl acetate/hexanes) to provide 17 (6.7 g, 92%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ1.48 (m, 2H), 1.60 (m, 4H), 2.58 (m, 2H), 3.63 (m, 2H) 3.80 (s, 3H), 6.83 (d, 2H), 7.10 (d, 2H).

Workup

  1. filtrationAfter this time, the mixture was filtered through a silica gel pad
  2. customthe solvent was removed at reduced pressure
  3. customThe residue was purified by flash chromatography (silica gel, 1:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-114306deb5744f5a827d9dfe52c8a547
Source dataset
uspto-grants-2005_02
Patent number
US06858614B2

Reaction notes

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