Sodium sulfate decahydrate → 2-(2-Methylquinolin-7-yl)propane-1,3-diol

HRID 339076Notes

Reaction equation

HRID 339076 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([C:24](OCC)=[O:25])[C:19](OCC)=[O:20])=[CH:13][CH:14]=2)[N:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOCC>[CH3:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([CH2:24][OH:25])[CH2:19][OH:20])=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 70984111Diethyl 2-(2-methylquinolin-7-yl)malonate

Product 1

HCID 709837452-(2-Methylquinolin-7-yl)propane-1,3-diolYield 41%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.0 N LAH (15.3 mL, 15.3 mmol) in THF was added diethyl 2-(2-methylquinolin-7-yl)malonate (1.15 g, 3.82 mmol) in Ether (30 mL) slowly at 0° C. The reaction mixture was stirred at 0° C. for 2 hours. Sodium sulfate decahydrate (2.0 g) was added and stirred at ambient temperature for 30 minutes. The solid was removed by filtration and washed with ethyl acetate (50 mL). The filtrate was concentrated and the residue obtained was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 40M column, 0-70% CH3CN/water gradient; 30 CV) to give 2-(2-methylquinolin-7-yl)propane-1,3-diol (0.34 g, 1.56 mmol, 41.0% 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 (50 mL)
  4. concentrationThe filtrate was concentrated
  5. customthe residue obtained
  6. customwas purified by C-18 reverse phase flash chromatography (Biotage SP4 unit

Sources & evidence

ORD record
ord-c17a68cf22244f08804d5565569d321b
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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