Methyl Benzoate → 4-(2-Quinolin-2-yl-ethyl)-benzoic acid methyl ester

HRID 33864

Reaction equation

HRID 33864 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Na+].[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH:23]=O.[CH2:25]1COCC1>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][C:7]([CH2:25][CH2:23][C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:13]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 7150Methyl BenzoateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 796192-Quinolinecarboxaldehyde

Product 1

HCID 685758694-(2-Quinolin-2-yl-ethyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[Triphenyl-phophanyl)-methyl]-benzoic acid methyl ester (1.87 g) in THF (16 ml) under N2 atmosphere at 0° C. was added sodium hydride (165 mg (60%)). After 30 min, quinoline-2-carbaldehyde (0.50 g) was added and the reaction stirred at ambient temperature for 2 h. The reaction mixture was quenched with brine, extracted with chloroform, dried magnesium sulfate, filtered and concentrated to provide the crude alkene. The crude product was placed on a parr shaker in ethanol (15 ml) with palladium hydroxide (200 mg) as the catalyst under 10 PSI of H2. After 40 min, the reaction mixture was filtered through celite and concentrated. Biotage MPLC chromatography eluting with 10-20% ethyl acetate/hexane provided the title compound. MS: (M+H m/z=292.1).

Workup

  1. customThe reaction mixture was quenched with brine
  2. extractionextracted with chloroform, dried magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide the crude alkene
  6. waitAfter 40 min
  7. filtrationthe reaction mixture was filtered through celite and
  8. concentrationconcentrated
  9. washBiotage MPLC chromatography eluting with 10-20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-68e438b175834339a48d1f36eaa20468
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

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