Tetramethylpyrazine → HCID 54378255, compound

HRID 1681793Notes

Reaction equation

HRID 1681793 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].[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([CH:25]=[CH:26][CH:27]=[O:28])=[CH:23][CH:22]=1>O1CCCC1>[OH:28][CH:27]([CH:26]=[CH:25][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:30][CH:29]=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 14296TetramethylpyrazineHCID 2309953-(4-Methoxyphenyl)prop-2-enalHCID 2724682Lithium diisopropylamide

Product 1

HCID 54378255HCID 54378255, 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 p-methoxycinnamaldehyde (17.8 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-7e4226f633b34ddaa7cc8c065c3580ed
Source dataset
uspto-grants-1992_12
Patent number
US05174308

Reaction notes

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