Water → methyl 5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazine-2-carboxylate

HRID 2192920Notes

Reaction equation

HRID 2192920 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>ClCCl>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:1][CH2:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59571042Methyl 5-(2-hydroxyethyl)pyrazine-2-carboxylate

Product 1

HCID 59571027methyl 5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-(2-hydroxyethyl)pyrazine-2-carboxylate (1.07 g) in dichloromethane (20 mL) were added 3,4-dihydro-2H-pyrane (1.6 mL) and pyridinium p-toluenesulfonate (295 mg) at room temperature, followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:2) to obtain methyl 5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazine-2-carboxylate (1.25 g) as a pale yellow oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe crude product obtained by concentration
  5. customwas purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:2)

Sources & evidence

ORD record
ord-6ccb58d61950406d94d039d27e23ae14
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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