Ethyl tetrahydro-2H-pyran-2-ylacetate → 2-(Oxan-2-yl)ethan-1-ol
Reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[O:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[CH2:5][CH2:4][OH:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (tetrahydro-pyran-2-yl)-acetic acid ethyl ester (77.1 g, 0.45 mol) in tetrahydrofuran (1.5 L) at 0° C. was added lithium aluminium hydride (22.1 g, 0.58 mol) in several portions. The mixture was stirred at 0° C. for 2 h and quenched with 1 N sodium hydroxide solution. The mixture was filtered and the filter cake was washed with dichloromethane (4×300 mL). The combined organic layers were concentrated in vacuo. The crude product was purified by distillation under reduced pressure to afford 2-(tetrahydro-pyran-2-yl)-ethanol (53.5 g, 92% yield) as a colorless oil.
Workup
- customquenched with 1 N sodium hydroxide solution
- filtrationThe mixture was filtered
- washthe filter cake was washed with dichloromethane (4×300 mL)
- concentrationThe combined organic layers were concentrated in vacuo
- distillationThe crude product was purified by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-c2f9cc581ad140d2a5937e4412518ebf
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222416B2
Reaction notes
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