Hydrochloric Acid → 1-[5-(1-Methylethoxy)pyridin-2-yl]ethanol

HRID 1038542

Reaction equation

HRID 1038542 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[O:12])=[N:9][CH:10]=1)[CH3:3].[CH3:13][Mg]Br.Cl>O1CCCC1>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:12])[CH3:13])=[N:9][CH:10]=1)[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 797940465-IsopropoxypicolinaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 665985281-[5-(1-Methylethoxy)pyridin-2-yl]ethanolYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-(1-Methylethoxy)picolinaldehyde (24 mg, 0.145 mmol) was dissolved in tetrahydrofuran (1.5 mL), added methylmagnesium bromide (230 μL, 0.218 mmol) under ice-cold conditions, and the mixture was stirred at 0° C. for 0.5 hours. The mixture was further stirred at room temperature for 0.5 hours. The reaction solution was added 1N aqueous solution of hydrochloric acid and an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and 1-[5-(1-methylethoxy)pyridin-2-yl]ethanol (27 mg (yield 98%)) was obtained as a brown oil.

Workup

  1. stirringThe mixture was further stirred at room temperature for 0.5 hours
  2. extractionan aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1dadb22347164d7591c719642af44734
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Linked notes

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