Tetrahydrofuran → 2-(2-Methoxy-3-pyridinyl)ethanol

HRID 1837704Notes

Reaction equation

HRID 1837704 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:10](O)=[O:11])=[CH:7][CH:6]=[CH:5][N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][OH:11])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 226783192-Methoxy-3-pyridineacetic acid

Product 1

HCID 140623082-(2-Methoxy-3-pyridinyl)ethanolYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.4 g of (2-methoxy-3-pyridyl)acetic acid, 550 mg of lithium aluminum hydride and 20 ml of THF were stirred at room temperature for 0.5 hour. 0.27 ml of water, 3.9 ml of a 3.8N aqueous sodium hydroxide and 0.78 ml of water were successively added thereto, and the resulting solid was filtered off. The filtrate was evaporated, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1, subsequently 1:1), to give 1.2 g of a yellow oil.

Workup

  1. filtrationthe resulting solid was filtered off
  2. customThe filtrate was evaporated
  3. customthe residue was purified by silica gel chromatography (hexane

Sources & evidence

ORD record
ord-1f5f935e8a8a4cf991801daa2511d6f5
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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