Quinoline → (Z)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-hex-4-enoic acid methyl ester

HRID 2070574Notes

Reaction equation

HRID 2070574 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8].N1C2C(=CC=CC=2)C=CC=1.[H][H]>C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:13][CH:14]=1)/[CH:6]=[CH:7]\[CH3:8]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 577714303-[4-(Tetrahydropyran-2-yloxy)-phenyl]-hex-4-ynoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 57771537(Z)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-hex-4-enoic acid methyl esterYield 93.5%

Reagents, catalysts & solvents 2

HCID 17887766Palladium barium sulphateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[4-(tetrahydropyran-2-yloxy)-phenyl]-hex-4-ynoic acid methyl ester (4.07 g) obtained in Step 1 in ethyl acetate (70 mL) were added successively quinoline (1.52 mL) and 5% palladium-barium sulfate (0.4 g), followed by stirring the reaction mixture under normal pressure in an atmosphere of hydrogen at room temperature for 15.5 hours. Then, after the reaction mixture was filtered through Celite, water and 1N aqueous hydrochloric acid solution were added to the filtrate, followed by extraction with ethyl acetate. The organic layer was washed successively with 1N aqueous hydrochloric acid solution and saturated brine, dried and concentrated to give (Z)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-hex-4-enoic acid methyl ester (3.83 g).

Workup

  1. filtrationThen, after the reaction mixture was filtered through Celite, water and 1N aqueous hydrochloric acid solution
  2. additionwere added to the filtrate
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed successively with 1N aqueous hydrochloric acid solution and saturated brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d3071f3305c54ec8b1efa21cce909333
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

Loading…