Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 5-chloropyrazine-2-carboxylate | HCID 406081 | — |
| Reactant | HCID 59571047 | HCID 59571047 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 59571074 | HCID 59571074 | 40.5% |
Reaction Steps
To a solution of 2-[(4-methoxybenzyl)oxy]-2-methylpropan-1-ol (0.30 g) in N-methylpyrrolidone (4.5 mL) was added sodium hydride (63 mg) under ice-cooling, followed by stirring at 60° C. for 30 minutes. To the reaction mixture was added methyl 5-chloropyrazine-2-carboxylate (246 mg), followed by stirring at 120° C. overnight. To the reaction mixture was added 1 M hydrochloric acid for neutralization in an ice bath, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to obtain methyl 5-{2-[(4-methoxybenzyl)oxy]-2-methylpropoxy}pyrazine-2-carboxylate (0.20 g) as a colorless oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08329707B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-aadb7a2bd79248b689bbc37b1509be25 |
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| Source note | uspto-grants-2012_12 |
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