Sodium borohydride → 2-(Oxan-2-yl)ethan-1-ol
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH:8]=[O:9].[BH4-].[Na+]>C(O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of tetrahydro-2H-pyran-2-ylacetaldehyde (528 mg) in ethanol (5 mL) was added sodium borohydride granules (156 mg). The mixture was heated at 50° C. for 2 h under nitrogen. After cooling, the solvent was evaporated and the residue treated with brine. The mixture was acidified by careful addition of 2N HCl and this mixture was extracted with DCM (×3). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound as a clear oil (465 mg).
Workup
- temperatureAfter cooling
- customthe solvent was evaporated
- additionthe residue treated with brine
- additionThe mixture was acidified by careful addition of 2N HCl
- extractionthis mixture was extracted with DCM (×3)
- washThe combined organics were washed with brine
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-542488229d6947f593ff7a4b25fde9ec
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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