4-Quinolinecarboxaldehyde → 1-(Quinolin-4-yl)ethanol

HRID 1836296Notes

Reaction equation

HRID 1836296 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[O:12])=[CH:3][CH:2]=1.[Li][CH3:14]>CCOCC>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]([OH:12])[CH3:14])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 780724-QuinolinecarboxaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 53147551-(Quinolin-4-yl)ethanolYield 64.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 4-quinolinecarbaldehyde (2 g, 12.73 mmol) in 20 ml anhydrous ether, MeLi (1.4M, 10 ml, 13.9 mmol) was added dropwise over a period of five minutes at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The solution was partitioned between ether (20 ml) and water (10 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to give 1.43 g (59%) of the product which was then used as such for the subsequent step.

Workup

  1. customThe solution was partitioned between ether (20 ml) and water (10 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c81d0e82aa7b4805a7248e56e74689d6
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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