Ethyl Acetate → 2-(2-Ethyl-1,3-dioxolan-2-yl)ethan-1-ol
Reaction equation
[CH2:1]([C:3]1([CH2:8][C:9](OC)=[O:10])[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C>C1COCC1>[CH2:1]([C:3]1([CH2:8][CH2:9][OH:10])[O:7][CH2:6][CH2:5][O:4]1)[CH3:2]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
To a solution of methyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetate (1 g, 5.75 mmol) in anhydrous THF (40 mL) was added LAH (900 mg, 23.7 mmol) at 0° C. under nitrogen atmosphere, the resulting mixture was stirred at 90° C. overnight. The mixture was cooled to room temperature, and ethyl acetate was added to the mixture. The resulting slurry was filtered and the filtrate was concentrated to dryness. The crude product was purified by silica gel chromatography eluting with DCM/methanol (100:1 to 20:1) to give 2-(2-ethyl-1,3-dioxolan-2-yl)ethanol (233 mg, 27.4%) as yellow oil that was used without purification.
Workup
- temperatureThe mixture was cooled to room temperature
- filtrationThe resulting slurry was filtered
- concentrationthe filtrate was concentrated to dryness
- customThe crude product was purified by silica gel chromatography
- washeluting with DCM/methanol (100:1 to 20:1)
Sources & evidence
- ORD record
- ord-a3ea0c00eed240358c5ab40bec1d22c9
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359359B2
Reaction notes
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