Ethanol → 2-(2-ETHOXYPYRIDIN-3-YLOXY)ETHANOL
Reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][Si](C(C)(C)C)(C)C)=[CH:6][CH:5]=[CH:4][N:3]=1.[O-:19][CH2:20][CH3:21].[Na+].CCO>>[CH2:20]([O:19][C:2]1[C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:21]Participants
4
Conditions
- Temperature
- 70 °C
Procedure
The product obtained in Step 1 above (13.2 g, 39.7 mmol) was added to sodium ethoxide in EtOH [prepared from Na (10.5 g, 457 mmol) and EtOH (200 mL)]. The resulting mixture was heated at 70° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with ice water (0.8 L) and extracted with EtOAc (×4). The combined organic phases were washed twice with brine, dried (MgSO4) and concentrated. The resulting dark red oil was purified by column chromatography on silica using toluene/Et3N (95:5), followed by (90:10), as eluent to give 3.0 g (41%) of the title product as a red oil. HRMS m/z calcd for C9H13NO3 (M)+183.0896. Found: 183.0895.
Workup
- temperatureAfter cooling to ambient temperature
- extractionextracted with EtOAc (×4)
- washThe combined organic phases were washed twice with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe resulting dark red oil was purified by column chromatography on silica
Sources & evidence
- ORD record
- ord-31743a51b6504dc4aba84a0f0347480d
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071180B2
Reaction notes
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