HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 5-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- | HCID 6425754 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 5-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridine | HCID 22473222 | — |
Reaction Steps
The reaction was carried out as described in Example 1, Step 3 using 2-bromo-5-(tert-butyldimethylsilyloxymethyl)pyridine (12 g, 39.7 mmol), BuLi (37 ml of a 1.6 M solution in hexanes, 59.6 mmol) DMF (9.2 ml, 0.12 mol) and NaBH4 (1.5 g, 39.7 mmol) to yield, after column chromatography on silica using Et2O as eluent, the title alcohol (6.66 g, 66%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06900209B2 |
| Source dataset | uspto-grants-2005_05 |
| ORD ID | ord-e7ab6a179a474464b0422f9fdeb6c6e9 |
| Source note | uspto-grants-2005_05 |