3-Phenylprop-2-Enal → HCID 54038795, compound

HRID 1587487Notes

Reaction equation

HRID 1587487 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[N:12][C:11]=1[CH3:18].[CH:19](=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[OH:28][CH:19]([CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:18][C:11]1[C:10]([CH3:9])=[N:15][C:14]([CH3:16])=[C:13]([CH3:17])[N:12]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 14296TetramethylpyrazineHCID 2724682Lithium diisopropylamide

Product 1

HCID 54038795HCID 54038795, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of lithium diisopropylamide (1.5 Molar, 73.3 mL, 0.11 mole) in 150 mL of tetrahydrofuran at -78° C. is added slowly a solution of tetramethylpyrazine (13.6 g, 0.1 mole) in 100 mL of tetrahydrofuran. The mixture is allowed to warm to room temperature and then cooled to -78° C. A solution of cinnamaldehyde (14.5 g, 0.11 mole) in 100 mL of tetrahydrofuran is added dropwise over 15 minutes. The reaction product mixture is then worked up according to the procedures of Example I to provide the title compound.

Workup

  1. temperaturecooled to -78° C

Sources & evidence

ORD record
ord-17b537b130da4e109e5c7975a59adc4d
Source dataset
uspto-grants-1993_06
Patent number
US05218118

Reaction notes

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