Water → HCID 57815288, compound
Reaction equation
[CH2:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([CH2:10][O:11]COC)=[CH:5][N:4]=1)[CH3:2].O.[OH-].[Na+].C(=O)([O-])O.[Na+]>O1CCOCC1.Cl.C(OCC)(=O)C>[CH2:1]([C:3]1[N:4]=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][C:8]=1[F:9])[CH3:2]Participants
Conditions
- Temperature
- 35 °C
Procedure
To a solution of 0.11 g of 2-ethyl-3-fluoro-5-((methoxymethoxy)methyl)pyridine in 2 mL of 1,4-dioxane, 1 mL of 6 mol/L hydrochloric acid was added, and the mixture was stirred at 30 to 40° C. for 1 hour. After cooling to room temperature, the reaction mixture was charged with water and ethyl acetate and adjusted to pH 7.9 with a 20% aqueous sodium hydroxide solution and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 87 mg of (6-ethyl-5-fluoropyridin-3-yl)methanol as a light yellow oily substance.
Workup
- temperatureAfter cooling to room temperature
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washthe resultant solution was washed with water
- dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-8eda70c621204ac39ac3f9baa95aca1d
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367831B2
Reaction notes
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