Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Chloro-3-(methoxymethoxy)pyridine | HCID 22020974 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 22020921 | HCID 22020921 | 54.2% |
Reaction Steps
Under nitrogen atmosphere. 2-propen-1-ol (0.002 mol) was added dropwise to a stirred mixture of NaH 60% (0.002 mol) in DME (5ml). The mixture was stirred at room temperature for 15 minutes. A solution of 3-(methoxymethoxy)-4-chloropyridine (0.0017 mol) in DME (5 ml) was added dropwise. The resulting reaction mixture was stirred at reflux overnight. The mixture was washed with water and extracted with ethyl acetate. The organic layer was dried, filtered and evaporated till dryness. The residue was purified by open column chromatography (eluent: hexane/ethyl acetate 3/2; CH2Cl2/2-propanone 90/10; CH2Cl2/MeOH 96/4). The product fractions were collected and the solvent was evaporated, yielding 0.18 g of 3-(methoxymethoxy)-4-(2-propenyloxy)pyridine (intermediate 7).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07081453B2 |
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| Source dataset | uspto-grants-2006_07 |
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| ORD ID | ord-55ae6d3dbf894db8b54952ca5af88cf3 |
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| Source note | uspto-grants-2006_07 |
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