HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → (5-[1,3]Dioxolan-2-yl-pyridin-2-yl)-methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 5-(1,3-Dioxolan-2-yl)picolinaldehyde | HCID 59255173 | — |
| Solvent | Water | HCID 962 | — |
| Product | (5-[1,3]Dioxolan-2-yl-pyridin-2-yl)-methanol | HCID 59255267 | 78.3% |
Reaction Steps
To an ethanol (20 mL) and tetrahydrofuran (20 mL) solution of 5-[1,3]dioxolan-2-yl-pyridine-2-carbaldehyde (1.73 g, 9.66 mmol) described in Manufacturing Example 154-1-3 was added sodium borohydride (731 mg, 19.3 mmol), which was stirred for 25 minutes at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:2) to obtain the title compound (1.37 g, 78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07691882B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-d266718a90e54b27b5a44492e4448e40 |
| Source note | uspto-grants-2010_04 |