3-Phenylprop-2-Enal → HCID 69903377, compound

HRID 1530886Notes

Reaction equation

HRID 1530886 reaction equation
[C:1]([NH:7][C:8]1[C:9]2[N:10]([C:14]([CH3:18])=[C:15]([CH3:17])[N:16]=2)[CH:11]=[CH:12][CH:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C([Li])(C)(C)C.[CH:24](=[O:33])[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCCCC.C(OCC)C>[CH3:17][C:15]1[N:16]=[C:9]2[C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[C:13]([CH:24]([OH:33])[CH:25]=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:12]=[CH:11][N:10]2[C:14]=1[CH3:18]

Participants

6

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 21873970HCID 21873970, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 69903377HCID 69903377, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

A vigorously stirred solution of 41 g of 8-pivaloylamino-2,3-dimethylimidazo[1,2-a]pyridine is treated dropwise at −78° C. under argon protective gas with 320 ml of a commercially available, 1.5 molar solution of t-butyllithium in n-pentane such that the temperature does not exceed −70° C. After stirring at −78° C. for a further 15 min, a solution of 61 g of cinnamaldehyde in 50 ml of dry diethyl ether is added dropwise (internal temperature <−68° C.). The mixture is then allowed to warm to room temperature, and is poured cautiously onto ice water and extracted three times with a total of 500 ml of ethyl acetate, the reddish-colored, organic phase is washed with distilled water and dried over sodium sulfate, and the solvent is stripped off in vacuo. The residual, yellowish suspension is treated with diethyl ether. The crystals obtained are filtered off with suction. 30 g of 2,3-dimethyl-7-(3-phenyl-1-hydroxy-2-propenyl)-8-pivaloylaminoimidazo[1,2-a]pyridine of melting point 194-5° C. are obtained.

Workup

  1. customdoes not exceed −70° C
  2. temperatureto warm to room temperature
  3. additionis poured cautiously onto ice water
  4. extractionextracted three times with a total of 500 ml of ethyl acetate
  5. washthe reddish-colored, organic phase is washed with distilled water
  6. dry with materialdried over sodium sulfate
  7. additionThe residual, yellowish suspension is treated with diethyl ether
  8. customThe crystals obtained
  9. filtrationare filtered off with suction

Sources & evidence

ORD record
ord-e199437f67414f89b10a443cc542f7f7
Source dataset
uspto-grants-2001_03
Patent number
US06197783B1

Reaction notes

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