Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 3-Cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol | HCID 67084717 | — |
| Reactant | 2-Bromo-4-(methylsulfonyl)thiophene | HCID 67484405 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 69059481 | HCID 69059481 | — |
Reaction Steps
Add 2-bromo-4-methanesulfonyl-thiophene (241 mg, 1.0 mmol), caesium fluoride ( 304 mg, 2.0 mmol) and tetrakis-(triphenylphosphin)-palladium(0) (58 mg, 0.05 mmol) to a solution of 3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (252 mg, 1.0 mmol) in THF. Stir at 50° C. for 24 h, monitore completion of the reaction by LCMS. Treat the reaction mixture with water and extract with ethyl acetate. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 405 mg crude product. Purify by silica gel chromatography, eluting with gradient from 9:1 to 1:1 hexane:ethyl acetate to obtain 118 mg purified product. MS (m/e): 309.0 (M+Na).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07576108B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-c51b99adf5324355a8e16c09c68d36f5 |
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| Source note | uspto-grants-2009_08 |
|---|