HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 2-Cyano-5-hydroxymethylpyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 6-Cyanopyridine-3-carboxylic acid | HCID 2761108 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Cyano-5-hydroxymethylpyridine | HCID 12251966 | 36.8% |
Reaction Steps
To a solution of 6-cyanonicotinic acid (12 g, 0.081 mol; see step (i) above) in THF at 0° C., Et3N (12.4 mL, 0.0892 mol) was added followed by ethyl chloroformate (8.53 mL, 0.0892 mol). The reaction mixture was stirred for 15 min and NaBH4 (6.14 g, 0.162 mol) was added. Then the mixture was stirred at RT overnight, quenched with water and extracted with methylene chloride. The organic layer was concentrated and purified by column chromatography to yield 4 g (20%) of the alcohol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07645751B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-d3f66a429a8043479778b68b73f7d06f |
| Source note | uspto-grants-2010_01 |