HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 3-Fluoro-2-(1-trityl-1H-imidazol-4-yl)benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Methyl 3-fluoro-2-(1-trityl-1H-imidazol-4-yl)benzoate | HCID 70874744 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | 3-Fluoro-2-(1-trityl-1H-imidazol-4-yl)benzaldehyde | HCID 89052954 | — |
Reaction Steps
To a solution of methyl 3-fluoro-2-(1-trityl-1H-imidazol-4-yl)benzoate (62 mg, 0.134 mmol) in toluene (4 mL) at −78° C. was added dropwise a solution DIBAH (1 M, 0.161 mL, 0.161 mmol) Stirring was continued at for 10 min. At this temperature, dry methanol was added. The mixture was poured into saturated aqueous NH4Cl (5 mL), diluted with EtOAc (15 mL), shaken vigorously for 3 min, added brine (5 mL), shaken again, the phases separated and the organic layer dried over Na2SO4, filtered, and evaporated to give the desired aldehyde which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09260434B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-ba53e2c1376e4664ba7aea1dd6575aa3 |
| Source note | uspto-grants-2016_02 |