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

HRID 1597363Notes

Reaction equation

HRID 1597363 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 tor 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-6eb32150d70c41e5ad6cbef956406831
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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