Water → 2-chloro-6-[1-(3-fluorophenyl)ethoxy]pyrazine

HRID 1357564Notes

Reaction equation

HRID 1357564 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:16]([OH:18])[CH3:17])[CH:13]=[CH:14][CH:15]=1.[H-].[Na+].O>O1CCOCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:18][CH:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=2)[CH3:17])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 953483-Fluoro-alpha-methylbenzenemethanol

Product 1

HCID 113911202-chloro-6-[1-(3-fluorophenyl)ethoxy]pyrazineYield 108.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,6-dichloropyrazine (298 mg, 2.00 mmol) and 1-(3-fluorophenyl)ethanol (308 mg, 2.2 mmol) in dioxane (5 mL) was added NaH (55% in oil, 96 mg, 2.2 mmol) at room temperature. The reaction mixture was stirred over night. Water (0.5 mL) was added and the mixture was stirred for 15 min. Drying (K2CO3), filtration, and concentration in vacuo gave the title compound as an oil (0.55 g) that was used directly in the next step. MS m/z 254 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. customDrying
  3. filtration(K2CO3), filtration, and concentration in vacuo

Sources & evidence

ORD record
ord-dda90a22b81e48b58526d018301c6296
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

Loading…