HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → trans-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | trans-Ethyl 2-(5-fluoro-2-methyl-2h-indazol-4-yl)cyclopropanecarboxylate | HCID 131729435 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | trans-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanol | HCID 66720702 | 90% |
Reaction Steps
To a solution of trans-ethyl 2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropanecarboxylate (2.00 g, 7.63 mmol) in tetrahydrofuran (76 mL) was slowly added a solution (1 M, 22.9 ml, 22.9 mmol) of diisobutylaluminum hydride in hexane at −78° C., and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (1.51 g, yield 90%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08110585B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-f89afb7bf7d24d0f9521bd3a37a71ef7 |
| Source note | uspto-grants-2012_02 |