Diisopropylamine → 2-(2-Hydroxy-2-p-methoxyphenylethyl)-6-methylpyrazine

HRID 1632273Notes

Reaction equation

HRID 1632273 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([CH3:20])[N:15]=1.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1>CCOCC.CCCCCC.O>[OH:28][CH:27]([C:26]1[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=1)[CH2:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([CH3:20])[N:15]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 79382,6-DimethylpyrazineHCID 312444-MethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 5727552-(2-Hydroxy-2-p-methoxyphenylethyl)-6-methylpyrazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

A solution of 5.05 grams (50 mmole) of diisopropylamine in 40 milliliters of ether was added to 47.1 mmole butyllithium in hexane at 0° C. After stirring the resulting solution for 15 minutes, 5.4 grams (50 mmole) of 2,6-dimethylpyrazine in 50 milliliters of ether were added slowly and the reaction mixture was stirred at 0° C. for 30 minutes. A solution of 5.4 grams (40 mmole) of p-methoxybenzaldehyde in 40 milliliters of ether was added, and stirring at 0° C. was continued for an additional 30 minutes. Water was added, the organic phase was separated, washed with water and dried over magnesium sulfate.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 30 minutes
  2. stirringstirring at 0° C.
  3. waitwas continued for an additional 30 minutes
  4. customthe organic phase was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-84b1f380d7f04baba603fe1d1677c085
Source dataset
uspto-grants-1984_10
Patent number
US04474819

Reaction notes

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