HCID 288419, compound → HCID 22064881, compound

HRID 1828046Notes

Reaction equation

HRID 1828046 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[CH:7]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:12][C:8]1[CH:7]=[C:6]([CH2:5][CH2:4][OH:3])[CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 288419HCID 288419, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22064881HCID 22064881, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2-methyl-pyridin-4-yl)-acetic acid ethyl ester (3.75 g, 20.2 mmol) in 100 mL of THF was cooled in an ice bath and a 1.0M solution of LAH in THF was added (15.7 mL, 15.7 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was cooled in an ice bath and quenched with the successive addition of water, 15% aqueous sodium hydroxide solution and additional water. The resulting mixture was stirred at room temperature for 1 hour then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give 2.8 g of the title compound as a light brown oil. MS(ES): m/e (EI*) 138.1 [M+H]

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customquenched with the successive addition of water, 15% aqueous sodium hydroxide solution and additional water
  3. stirringThe resulting mixture was stirred at room temperature for 1 hour
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-75135cdb02c94bb38aebcd870c882c7c
Source dataset
uspto-grants-2006_06
Patent number
US07056937B2

Reaction notes

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