Sodium Hydroxide → 2-(5,6,7,8-Tetrahydroquinolin-2-yl)ethanol

HRID 920892Notes

Reaction equation

HRID 920892 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][C:8]=1[CH2:17][C:18](OCC)=[O:19].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[N:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][C:8]=1[CH2:17][CH2:18][OH:19]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 86683110Ethyl 2-(5,6,7,8-tetrahydroquinolin-2-yl)acetate

Product 1

HCID 866831112-(5,6,7,8-Tetrahydroquinolin-2-yl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Under N2, 4.56 mL (4.56 mmol) of lithium aluminium hydride (1M in THF) was cooled to 0° C. and ethyl 2-(5,6,7,8-tetrahydroquinolin-2-yl)acetate (1 g, 4.56 mmol) dissolved in a small quantity of THF was slowly added. The mixture was allowed to stir for 1.5 h. To the reaction mixture 173 mg of H2O in THF, 173 mg of 10% ige NaOH and 3×173 mg of H2O were added. The mixture was then stirred for 30 min. Magnesium sulfate was added. After removal of the solvent, the crude product (0.78 g, 96%) was purified by chromatography (eluent: EA/heptane 3/1) to give the title compound.

Workup

  1. additionwas slowly added
  2. stirringThe mixture was then stirred for 30 min
  3. customAfter removal of the solvent
  4. customthe crude product (0.78 g, 96%) was purified by chromatography (eluent: EA/heptane 3/1)

Sources & evidence

ORD record
ord-c83ea69c3e7e414e9d2b2beb773bcce8
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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