Sodium Sulfate → (1,2,3,4-Tetrahydroquinolin-2-yl)methanol

HRID 1881677Notes

Reaction equation

HRID 1881677 reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][CH:6]1[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 338259ethyl 1,2,3,4-tetrahydroquinoline-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanolYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,2,3,4-Tetrahydroquinoline-2-carboxylic acid ethyl ester (4.75 g 25 mmol) in THF (5 ml/mmol) was added dropwise to a suspension of LAH (2 eq.) in THF (50 ml) at 0° C. The reaction mixture was stirred at RT for 1 h and then heated under reflux for 4 h. After addition of aqueous saturated Na2SO4 solution, the mixture was filtered and the organic solvent was removed in vacuo. The product was purified by column chromatography (silica gel, ethyl acetate/hexane 3:7). Yield: 50%

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. filtrationthe mixture was filtered
  4. customthe organic solvent was removed in vacuo
  5. customThe product was purified by column chromatography (silica gel, ethyl acetate/hexane 3:7)

Sources & evidence

ORD record
ord-8e5beeed1422482992b0c8c999a93319
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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