Tetrahydrofuran → Methyl (E)-3-(2-quinolinyl)-2-propenoate

HRID 1626366Notes

Reaction equation

HRID 1626366 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.C[C:14](P(OC)(O)=O)([C:16]([O-:18])=[O:17])C.[H-].[Na+].[CH2:26]1COCC1>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:14]/[C:16]([O:18][CH3:26])=[O:17]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 796192-QuinolinecarboxaldehydeHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 6479253Methyl (E)-3-(2-quinolinyl)-2-propenoate

Procedure

To a solution of 2-quinolinecarboxaldehyde (10 g, 64 mmol) in 200 mL THF was added trimethylphosphonoacetate (11.0 mL, 76 mmol) and then sodium hydride (3.05 g of a 60% suspension in oil, 76 mmol). After stirring for 3 h at room temperature, the reaction was quenched by the addition of a saturated ammonium chloride solution. The mixture was extracted twice with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was suspended in ˜75 mL Et2O and to that was added ˜125 mL hexanes and the mixture was placed in the freezer. The solids were collected by filtration to provide 8.46 g (62%) of G5 as a pale orange solid. MS (Electrospray): m/z 214.3 (MH+).

Workup

  1. customthe reaction was quenched by the addition of a saturated ammonium chloride solution
  2. extractionThe mixture was extracted twice with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionto that was added ˜125 mL hexanes
  8. filtrationThe solids were collected by filtration
  9. customto provide 8.46 g (62%) of G5 as a pale orange solid

Sources & evidence

ORD record
ord-1ccd5889f3b849c3ace9196106344e01
Source dataset
uspto-grants-2014_07
Patent number
US08785467B2

Reaction notes

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