Diethyl Ether → HCID 11579135, compound

HRID 911439Notes

Reaction equation

HRID 911439 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[CH2:9]([Mg]Br)[CH3:10].CCOCC>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([OH:8])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 142732-PyridinecarboxaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 11579135HCID 11579135, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-pyridine carboxaldehyde (4.0 g, 37.34 mmol) in THF (50 mL) at 0° C., add 3M ethyl magnesium bromide in ether (18.7 mL, 56.0 mmol), continue stirring for 30 min at 0° C. and then at ambient temperature for 2 h. Add water (200 mL), extract three times with EtOAc, dry over anhydrous Na2SO4, filter through a short pad of silica gel and concentrate in vacuo to give the desired intermediate as a yellow oil (3.39 g, 66%).

Workup

  1. waitat ambient temperature for 2 h
  2. extractionAdd water (200 mL), extract three times with EtOAc
  3. dry with materialdry over anhydrous Na2SO4
  4. filtrationfilter through a short pad of silica gel
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7a8778d3405a454c9a6968fa418aadb0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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