3-Phenylprop-2-Enal → 2-(2-Hydroxy-4-phenyl-3-buten-1-yl)-6-methylpyrazine

HRID 1681792Notes

Reaction equation

HRID 1681792 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[CH:15]=[N:14][CH:13]=[C:12]([CH3:16])[N:11]=1.[CH:17](=[O:26])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[OH:26][CH:17]([CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][C:10]1[CH:15]=[N:14][CH:13]=[C:12]([CH3:16])[N:11]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 79382,6-DimethylpyrazineHCID 2724682Lithium diisopropylamide

Product 1

HCID 544020952-(2-Hydroxy-4-phenyl-3-buten-1-yl)-6-methylpyrazine

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 2,6-dimethylpyrazine (10.8 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-a2105a15a7ed460e8b168f11e278a0f4
Source dataset
uspto-grants-1992_12
Patent number
US05174308

Reaction notes

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