3-(3-Quinolyl)-2-propyn-1-ol t-butyl carbonate → 3-(3-Quinolyl)-2-propen-1-ol t-butyl carbonate

HRID 1370014Notes

Reaction equation

HRID 1370014 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][OH:14])[CH:2]=1.[C:15]([O:19][C:20](=[O:22])[O-:21])([CH3:18])([CH3:17])[CH3:16]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].[Pd].C(O)(C)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:12][CH2:13][OH:14])[CH:2]=1.[C:15]([O:19][C:20](=[O:21])[O-:22])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 1

HCID 1317233963-(3-Quinolyl)-2-propyn-1-ol t-butyl carbonate

Product 1

HCID 865842593-(3-Quinolyl)-2-propen-1-ol t-butyl carbonate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 131709914Lindlars catalystCatalystHCID 3776IsopropanolSolvent

Procedure

To a 250 mL single-necked round-bottom flask was charged the 3-(3-quinolyl)-2-propyn-1-ol t-butyl carbonate (1.52 g, 5.37 mmol), isopropanol (30 mL) and 5% palladium on calcium carbonate poisoned with lead (Lindlar's catalyst, 75 mg, 0.049 equiv). The suspension was stirred (rapidly) magnetically and the atmosphere above the solution was purged with hydrogen. A balloon of hydrogen gas was then placed over the reaction stirring mixture and the reaction was allowed to stir for 16 hours at room temperature. The reaction mixture was then filtered through a 0.45μ filter disk and rinsed with 10 mL of isopropanol. The combined filtrates were concentrated under reduced pressure and the residue (1.55 g) was taken up in 9 mL of heptane/acetone (8:1) and eluted through a plug of silica gel (1.5 g) with 8:1:0.01 heptane/acetone/triethylamine. The desired fractions were combined and concentrated under reduced pressure to provide 3-(3-quinolyl)-2-propen-1-ol t-butyl carbonate: 1.1 g, 71.9%

Workup

  1. customwas purged with hydrogen
  2. stirringstirring mixture
  3. stirringto stir for 16 hours at room temperature
  4. filtrationThe reaction mixture was then filtered through a 0.45μ filter disk
  5. washrinsed with 10 mL of isopropanol
  6. concentrationThe combined filtrates were concentrated under reduced pressure
  7. washeluted through a plug of silica gel (1.5 g) with 8:1:0.01 heptane/acetone/triethylamine
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25c6bd31c54a4caf8df6b9cfe15ed5b2
Source dataset
uspto-grants-2003_06
Patent number
US06579986B2

Reaction notes

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