Sodium sulfate decahydrate → HCID 86707554, compound

HRID 339081Notes

Reaction equation

HRID 339081 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][C:13](OC)=[O:14])=[CH:7][CH:8]=2)[N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][CH2:13][OH:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 70984314Methyl 2-(2-methylquinolin-7-yl)acetate

Product 1

HCID 86707554HCID 86707554, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

methyl 2-(2-methylquinolin-7-yl)acetate (5.78 g, 26.9 mmol) in THF (50 mL) was added 1M LAH (40.3 mL, 40.3 mmol) in THF at 0° C., followed by stirring at 0° C. for 3 hours. Sodium sulfate decahydrate (10.0 g) was added and stirred at ambient temperature for 30 minutes. The solid was removed by filtration and washed with ethyl acetate (100 mL). The filtrate was concentrated and the residue obtained was purified by flash chromatography (ethyl acetate) on silica gel to give 2-(2-methylquinolin-7-yl)ethanol (2.35 g, 12.6 mmol, 47% yield) as a solid.

Workup

  1. stirringstirred at ambient temperature for 30 minutes
  2. customThe solid was removed by filtration
  3. washwashed with ethyl acetate (100 mL)
  4. concentrationThe filtrate was concentrated
  5. customthe residue obtained
  6. customwas purified by flash chromatography (ethyl acetate) on silica gel

Sources & evidence

ORD record
ord-1289f9ea5a8d4fa3bfaab04f9ec0bca8
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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