1-(6-Chloropyridin-3-yl)ethan-1-one → 2-(6-Chloropyridin-3-yl)propan-2-ol

HRID 1925128Notes

Reaction equation

HRID 1925128 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][Li]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])([CH3:11])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 125621182-(6-Chloropyridin-3-yl)propan-2-olYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(6-chloropyridin-3-yl)ethanone (2.0 g, 12.85 mmol) in THF (Volume: 25 mL) was added methyllithium (16.07 mL, 25.7 mmol) at 0° C. The reaction was stirred for 1 hr and allowed to warm to room temperature. The resulting deep red solution was quenched with water (Volume: 50 mL), extracted with EtOAc (1×50 mL), and the organic layer was dried over MgSO4. The organic phase was filtered and the filtrate was evaporated to dryness via rotary evaporation. The resulting material was purified via MPLC (DCM:MeOH, 95:5) to provide 2-(6-chloropyridin-3-yl)propan-2-ol (0.985 g, 5.74 mmol, 44.6% yield) as a dark red solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (s, 5 H) 5.32 (s, 1 H) 7.44 (d, J=8.34 Hz, 1 H) 7.90 (dd, J=8.34, 2.53 Hz, 1 H) 8.49 (d, J=2.53 Hz, 1 H). ESI-MS:m/z 172.0 (M+H)+.

Workup

  1. customThe resulting deep red solution was quenched with water (Volume: 50 mL)
  2. extractionextracted with EtOAc (1×50 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationThe organic phase was filtered
  5. customthe filtrate was evaporated to dryness via rotary evaporation
  6. customThe resulting material was purified via MPLC (DCM:MeOH, 95:5)

Sources & evidence

ORD record
ord-a591474eda8e4d0c940b800bbcf8510c
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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