Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ethyl 4,6-dichloropyridine-3-carboxylate | HCID 600045 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4,6-Dichloropyridine-3-carbaldehyde | HCID 21698042 | 65% |
Reaction Steps
To a solution of ethyl 4,6-dichloronicotinate (500 mg, 2.43 mmol) in DCM at −78° C., DIBAL-H (2.67 mL, 2.67 mmol) was added dropwise and stirred for 3 h at −78° C. The mixture was allowed to warm up to 0° C. then water (0.12 mL) was added dropwise to the mixture followed by aq. NaOH (15%, 0.12 mL). H2O (0.3 mL) was added then the mixture was warmed up to room temperature and stirred for 15 min and the organic layer collected, dried over MgSO4 and filtered with the filtrate concentrated to give the desired product with was used without further purification (280 mg, Yield 65%). LCMS (m/z): 176.1 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09388173B2 |
|---|
| Source dataset | uspto-grants-2016_07 |
|---|
| ORD ID | ord-f55e2f045b7b48f7a09c51bc41532c78 |
|---|
| Source note | uspto-grants-2016_07 |
|---|