Water → (5,6,7,8-Tetrahydroquinoxalin-2-yl)methanol
Reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=[CH:3][C:2]=1[C:11](OCC)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=[CH:3][C:2]=1[CH2:11][OH:12]Participants
Procedure
To a solution of 0.16 g of ethyl 5,6,7,8-tetrahydroquinoxaline-2-carboxylate in 1.5 mL of tetrahydrofuran, 29 mg of lithium aluminum hydride was added under cooling with ice, the mixture was stirred for 45 minutes, 29 mg of lithium aluminum hydride was further added thereto, and the mixture was stirred for 30 minutes. Thereto were added ethyl acetate and water, the insoluble substance was filtered off, sodium chloride was added to a filtrate, 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 a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.10 g of (5,6,7,8-tetrahydroquinoxalin-2-yl)methanol as a brown solid.
Workup
- temperatureunder cooling with ice
- stirringthe mixture was stirred for 30 minutes
- filtrationthe insoluble substance was filtered off
- additionsodium chloride was added to a filtrate
- customthe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washthe resultant solution was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-2d0fba4bd9834e19bb37820e8e16cc97
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211908B2
Reaction notes
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