Water → 2-(1,3-Benzodioxol-5-ylmethoxy)-6-chloropyrazine

HRID 1296607Notes

Reaction equation

HRID 1296607 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH2:9]([OH:19])[C:10]1[CH:18]=[CH:17][C:16]2[O:15][CH2:14][O:13][C:12]=2[CH:11]=1.[H-].[Na+].O>O1CCOCC1>[O:15]1[C:16]2[CH:17]=[CH:18][C:10]([CH2:9][O:19][C:2]3[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=3)=[CH:11][C:12]=2[O:13][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 10322Piperonyl alcoholHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

Product 1

HCID 181868062-(1,3-Benzodioxol-5-ylmethoxy)-6-chloropyrazineYield 102%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,6-dichloropyrazine (298 mg, 2.00 mmol) and piperonyl alcohol (335 mg, 2.20 mmol) in dioxane (5 mL) was added NaH (55% in mineral oil, 96 mg, 2.2 mmol) at room temperature. The reaction mixture was stirred overnight. Water (0.5 mL) was added and the mixture was stirred for 15 min. Drying, Na2CO3, filtration and concentration in vacuo furnished an oil (0.54 g) that was used directly in the next step. HRMS m/z calcd for C12H9ClN2O3 (M)+ 264.0302, found 264.0303.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. customDrying
  3. filtrationNa2CO3, filtration and concentration in vacuo

Sources & evidence

ORD record
ord-5d1b74f478c04b7e84b28318679630e2
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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