2-Chloroethanol → 1-(2-Hydroxyethyl)-3,5,6-trimethylpyrazin-2(1H)-one

HRID 1904326Notes

Reaction equation

HRID 1904326 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[C:4]([CH3:10])[N:3]=1.[OH-].[Na+].[C:13]([OH:17])(C)(C)[CH3:14].C(Cl)CO>O>[OH:17][CH2:13][CH2:14][N:3]1[C:4]([CH3:10])=[C:5]([CH3:9])[N:6]=[C:7]([CH3:8])[C:2]1=[O:1]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 178432813HCID 178432813, compound

Product 1

HCID 147735301-(2-Hydroxyethyl)-3,5,6-trimethylpyrazin-2(1H)-oneYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-Hydroxy-3,5,6-trimethylpyrazine (13.8 g, 0.1M) and 5N NaOH (100 ml, 0.5M) were added to t-butanol (200 ml). Ethylene chlorohydrin (40.3 g, 0.5M) was added thereto and the mixture was stirred at 60° C. for 2 hours. Water was added to the reaction mixture, which was then extracted 10 times with chloroform (100 ml), and the extract dried with anhydrous magnesium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (Wako Pure Chem. Co., C-200) and eluted with chloroform-methanol (300:1) to obtain the product (14.4 g, yield: 79.1%).

Workup

  1. extractionwas then extracted 10 times with chloroform (100 ml)
  2. dry with materialthe extract dried with anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. additionThe residue was charged on a column of silica-gel (Wako Pure Chem. Co., C-200)
  5. washeluted with chloroform-methanol (300:1)

Sources & evidence

ORD record
ord-290968a95535432492158b90947c070a
Source dataset
uspto-grants-1989_06
Patent number
US04837319

Reaction notes

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