Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,6-Dibromohexane | HCID 12368 | — |
| Reactant | 5-Hydroxy-2-{[(oxan-2-yl)oxy]methyl}-4H-pyran-4-one | HCID 13711789 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 17975811 | HCID 17975811 | 52% |
Reaction Steps
5-Hydroxy-2-(tetrahydro-pyran-2-yloxymethyl)-4H-pyran-4-one (1.50 g, 6.60 mmol) was charged in a 30 mL sealed tube equipped with a magnetic stirrer and under inert atmosphere. Anhydrous DMF (10 mL), Cs2CO3 (2.30 g, 7.00 mmol) and 1,6-dibromo-hexane (3.20 g, 13.30 mmol) were successively added. The reaction mixture was stirred 2 h at 60° C. After evaporation of DMF, the crude compound was purified by column chromatography (SiO2; CH2Cl2:EtOAc=8:2) to give after evaporation 5-(6-bromo-hexyloxy)-2-(tetrahydro-pyran-2-yloxymethyl)-4H-pyran-4-one 3 as an oil (190 mg, 52% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07514432B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-e284b0d15c4942e0979f08a9655100c1 |
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| Source note | uspto-grants-2009_04 |
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