Toluene → HCID 14360978, compound

HRID 1830830Notes

Reaction equation

HRID 1830830 reaction equation
C(C(CC)(CC)C[CH:5](P(O)(O)=O)[C:6]([O-:8])=[O:7])C.[H-].[Na+].[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29]=O.[C:31]1(C)C=CC=C[CH:32]=1>C1COCC1>[CH2:31]([O:8][C:6](=[O:7])/[CH:5]=[CH:29]/[C:20]1[CH:21]=[CH:22][C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:19]=1)[CH3:32]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 796192-QuinolinecarboxaldehydeHCID 92002048HCID 92002048, compound

Product 1

HCID 14360978HCID 14360978, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of triethyl-2-phosphonobutyrate (26.6 g, 118.7 mmol) in dry toluen (250 ml) was cooled on ice and added sodium hydride (60% in oil, 3.3 g, 134.6 mmol). After stirring at 0° C. for 20 min. a solution of quinolinecarboxaldehyde (12.5 g, 79.5 mmol) in dry THF (30 mL) was added. The mixture was slowly warmed to room temperature, and stirring continued for 24 h. The reaction mixture was quenched with ethanol and added water. The aqueous phase was extracted with dichloro methane (×2). The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The residue was submitted to flash chromatography, eluting with heptane graduated to heptane/ethyl acetate (4:1), to give 12.5 g (70%) of (E)-3-quinolin-2-yl-acrylic acid ethyl ester.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with ethanol
  3. additionadded water
  4. extractionThe aqueous phase was extracted with dichloro methane (×2)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washeluting with heptane

Sources & evidence

ORD record
ord-202e1f022306470a8f0c037244bdbbd5
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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