1-(2-Methylpyridin-3-yl)ethan-1-one → 2-(2-Methylpyridin-3-yl)propan-2-ol

HRID 250958Notes

Reaction equation

HRID 250958 reaction equation
[CH3:1][Mg+].[Br-].[CH3:4][C:5]1[C:10]([C:11](=[O:13])[CH3:12])=[CH:9][CH:8]=[CH:7][N:6]=1>CCOCC>[CH3:4][C:5]1[C:10]([C:11]([OH:13])([CH3:1])[CH3:12])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 109424821-(2-Methylpyridin-3-yl)ethan-1-oneHCID 178418689HCID 178418689, compound

Product 1

HCID 450917322-(2-Methylpyridin-3-yl)propan-2-olYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

MeMgBr (3.0 M in Et2O, 4.63 ml, 13.9 mmol) was added dropwise via syringe to a solution of 1-(2-methyl-pyridin-3-yl)-ethanone (1.88 g, 13.9 mmol) (Sanders et al. J. Org. Chem. 1978, 43, 324) in Et2O (60 mL) to give a white slurry. The mixture was refluxed for 16 h, cooled to room temperature, quenched with water (50 mL) and extracted with CH2Cl2 (7×60 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to afford a yellow oil. Purification via column chromatography on silica gel (CH2Cl2:MeOH, 95:5, v/v) afforded 2-(2-methyl-pyridin-3-yl)-propan-2-ol as a white crystalline solid (1.30 g, 62%). 1H NMR (CDCl3) δ 1.67 (s, 6H), 2.79 (s, 3H), 7.08 (m, 1H), 7.75 (d, 1H, J=7.5 Hz), 8.36 (d, 1H, J=3.0 Hz).

Workup

  1. customto give a white slurry
  2. temperatureThe mixture was refluxed for 16 h
  3. customquenched with water (50 mL)
  4. extractionextracted with CH2Cl2 (7×60 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow oil
  9. customPurification via column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-31d98ff72c65417f8e9bffa12f11e259
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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