Sodium Hydroxide → HCID 59634077, compound

HRID 1615081Notes

Reaction equation

HRID 1615081 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH:16]([C:22](OCC)=[O:23])[C:17](OCC)=[O:18])=[CH:9][CH:8]=1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH:16]([CH2:17][OH:18])[CH2:22][OH:23])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59634074HCID 59634074, compound2×

Product 1

HCID 59634077HCID 59634077, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of LiAlH4 (0.34 g) in THF (10 mL) was added a solution of diethyl 2-(3-pyridin-4-yl-propyl)-malonate (1.23 g) prepared in (2) in THF (5 mL) at 0° C. The reaction mixture was stirred at RT for 3 hr and at 50° C. for 2 hr. To the reaction mixture were added water (0.34 mL), aqueous 4 N NaOH (0.34 mL) and then water (1 mL) at 0° C. The mixture was stirred at RT for 30 min. Celite and Na2SO4 were added to the mixture. The mixture was filtered using Celite. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=9/1) to give the title compound (0.21 g, 24%).

Workup

  1. customat 0° C
  2. stirringThe mixture was stirred at RT for 30 min
  3. filtrationThe mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-efb13d398eae4c1685b01bd7ff0179cf
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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