2-Methylpyrazine → HCID 54431996, compound

HRID 1681794Notes

Reaction equation

HRID 1681794 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[CH:15]=[N:14][CH:13]=[CH:12][N:11]=1.[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([CH:22]=[CH:23][CH:24]=[O:25])=[CH:20][CH:19]=1>O1CCCC1>[OH:25][CH:24]([CH:23]=[CH:22][C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:27][CH:26]=1)[CH2:9][C:10]1[CH:15]=[N:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 79762-MethylpyrazineHCID 2309953-(4-Methoxyphenyl)prop-2-enalHCID 2724682Lithium diisopropylamide

Product 1

HCID 54431996HCID 54431996, 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 to a solution of 2-methylpyrazine (9.4 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 procedure of Example I to provide the title compound.

Workup

  1. temperaturecooled to -78° C

Sources & evidence

ORD record
ord-efd0ecd8fb18439b910e2b922fe20f0c
Source dataset
uspto-grants-1992_12
Patent number
US05174308

Reaction notes

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