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

HRID 443333

Reaction equation

HRID 443333 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 mole 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-b78624bf854a48b6ac2689b539b97161
Source dataset
uspto-grants-1981_04
Patent number
US04259969

Linked notes

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