Diethyl Ether → 1-(6-Methylpyridin-2-yl)ethanol

HRID 2041315Notes

Reaction equation

HRID 2041315 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][Mg]Br.CCOCC>C1COCC1>[OH:9][CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)[CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 3531381-(6-Methylpyridin-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-methylpyridine-2-carboxaldehyde (2.0 g, 16.5 mmol) in dry THF (55 mL) at 0° C. under nitrogen, add a solution of 3M methyl magnesium bromide in ether (6.0 mL, 18.0 mmol,) dropwise with stirring. After 1 h at 0° C., quench with saturated aqueous NH4Cl, extract three times with EtOAc, dry over anhydrous Na2SO4 and concentrate in vacuo to give the desired intermediate (crude, 2.3 g).

Workup

  1. customquench with saturated aqueous NH4Cl
  2. extractionextract three times with EtOAc
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1cc34507a3da4e9da58e05b0011727aa
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

Loading…