HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2075216Generated: November 1, 2026
Tetrahydrofuran → 5-Benzyl-2-methoxypyridine
https://huagongshe.com/reaction/2075216
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 5-Bromo-2-methoxypyridine | HCID 2734895 | — |
| Reactant | 9-Benzyl-9-borabicyclo(3.3.1)nonane | HCID 4150924 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 5-Benzyl-2-methoxypyridine | HCID 58415341 | — |
Reaction Steps
A sealable tube was charged with S-phos (0.22 g, 0.53 mmol), palladium acetate (0.060 g, 0.27 mmol), potassium phosphate (8.5 g, 40 mmol) and 5-bromo-2-methoxypyridine (1.8 mL, 13 mmol) under argon. 9-Benzyl-9-bora-bicyclo[3.3.1]nonane 0.5M in THF (53 mL, 27 mmol) was added, the vessel was sealed and heated to 60° C. overnight. The mixture was diluted with diethyl ether and was filtered through a pad of celite. Evaporation of the filtrate and purification by flash chromatography (0-40% EtOAc/hexanes) gave 5-benzyl-2-methoxypyridine. MS (ESI) m/z: Calculated: 199.1; Observed: 200.1 (M++1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07919519B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-5a2f00f4c2dc4180bd15b5ddf031ef9d |
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| Source note | uspto-grants-2011_04 |
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