Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Formylphenylboronic Acid | HCID 591073 | — |
| Reactant | 2-(4-Bromophenoxy)tetrahydro-2H-pyran | HCID 4646436 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86709388 | HCID 86709388 | 45.2% |
Reaction Steps
2-(4-Bromophenoxy)tetrahydropyran (3.0 g) was dissolved in N,N-dimethylformamide (30 ml). 4-Formylphenylboronic acid (2.1 g), tetrakis(triphenylphosphine)palladium (0) (1.35 g) and tripotassium phosphate (4.95 g) were added thereto, and the resulting mixture was heated at 90 to 100° C. under a nitrogen atmosphere for 3 hours. After completion of the reaction, ethyl acetate was added to the reaction mixture and filtered through Celite. The filtrate was separated into layers. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→50:50) to afford the title compound as a white powder (1.49 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051333B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-bca42a1e30f34756bbab683361151bba |
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| Source note | uspto-grants-2015_06 |
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