Methanol → Methyl 6-methoxypyrazine-2-carboxylate
Reaction equation
O[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[N:4][CH:3]=1.Cl[Si](C)(C)[CH3:13].C1COCC1.[CH3:21][OH:22]>>[CH3:21][O:22][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:13])=[O:9])[CH:5]=[N:4][CH:3]=1Participants
Procedure
To 0.42 g (0.003 mol) of 6-hydroxy-pyrazinoic acid suspended in 10 mL of anhydrous methanol was added 4 mL of (0.030 mol) of chlorotrimethylsilane. The resultant mixture was allowed to stir for 48 hours at room temperature during which time the suspension became a solution. It is expected that this procedure may be used to convert 6-hydroxypyrazinoic acid to any 6-alkoxypyrazinoic ester by the use of the appropriate alcohol and, when the alcohol is not a liquid, the use of an inert solvent such as THF. The solvent and excess chlorotrimethylsilane were removed in vacuo by rotary evaporation. The crude product was purified by column chromatography on silica gel with a hexane-ethyl acetate gradient to yield 0.11 g (22%) of methyl 6-methoxypyrazinecarboxylate.
Workup
- customThe solvent and excess chlorotrimethylsilane were removed in vacuo by rotary evaporation
- customThe crude product was purified by column chromatography on silica gel with a hexane-ethyl acetate gradient
Sources & evidence
- ORD record
- ord-22b06440797b43a5b4e71c6b5056f71f
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05643912
Reaction notes
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