HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 1-(Tetrahydrofuran-3-YL)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2774010 | — |
| Reactant | Oxolan-3-yl methanesulfonate | HCID 15278452 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-(Tetrahydrofuran-3-YL)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazole | HCID 59231712 | 71.9% |
Reaction Steps
A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.1 g, 0.5 mmol), sodium hydride (31 mg, 0.77 mmol) in N,N-dimethylformamide (1 mL, 10 mmol) was stirred at r.t. for 10 min, then, tetrahydrofuran-3-yl methanesulfonate (86 mg, 0.52 mmol) was added. The resulting mixture was stirred at 110° C. for 2 hours. After cooling it was diluted with ethyl acetate, washed with water twice, brine once; dried over Na2SO4. After filtration the filtrate was concentrated to yield 95 mg of product which was directly used in the next step reaction without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08436008B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-1948aef0078c4a13bf6ceaa30d630477 |
| Source note | uspto-grants-2013_05 |