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

HRID 458602Notes

Reaction equation

HRID 458602 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) δ 1.48 (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-fe49fe3fea824f5396fac8f863eca9e8
Source dataset
uspto-grants-2007_03
Patent number
US07192959B2

Reaction notes

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