Ethyl 3-(tetrahydro-2H-pyran-3-yl)propanoate → 3-(Oxan-3-yl)propan-1-ol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][CH2:14][C:15](OCC)=[O:16])[CH2:8]1>C(OCC)C>[O:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of lithium aluminium hydride (24.8 ml, 1.0M in diethyl ether) in dry diethyl ether (77 ml) at 0° C. was added a solution of ethyl 3-(tetrahydro-2H-pyran-3-yl)propanoate (4.61 g) in dry diethyl ether (77 ml) dropwise over 20 minutes. After 15 minutes at 0° C. the reaction mixture was warmed to room temperature and stirred for a further nine hours. The reaction was quenched by the dropwise addition of water over a period of one hour, whilst cooled over ice. The resulting solids were filtered from the mixture and washed with diethyl ether. The organic layer was decanted off from the aqueous layer, dried over magnesium sulphate, filtered and concentrated in vacuo. to give a clear oil (3.33 g). The product was purified by silica chromatography (40 g) (ISCO) using a gradient elution of 0-50% cyclohexane:ethyl acetate to afford the title compound as a clear oil (2.64 g).
Workup
- customThe reaction was quenched by the dropwise addition of water over a period of one hour
- temperaturewhilst cooled over ice
- filtrationThe resulting solids were filtered from the mixture
- washwashed with diethyl ether
- customThe organic layer was decanted off from the aqueous layer
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a2dfbc75f6ea4a59aea1ce887d05a503
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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