Hydrochloric Acid → 1-(Furo[2,3-c]pyridin-5-yl)ethanol

HRID 1038607Notes

Reaction equation

HRID 1038607 reaction equation
[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH3:12][Mg]Br.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]([OH:11])[CH3:12])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22047533Furo[2,3-c]pyridine-5-carboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 105112031-(Furo[2,3-c]pyridin-5-yl)ethanolYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, furo[2,3-c]pyridine-5-carbaldehyde (488 mg, 3.31 mmol) was dissolved in tetrahydrofuran (11 mL), and added methylmagnesium bromide (5.5 mL (1.0 M in THF solution), 4.97 mmol) under ice-cold conditions. Then, the mixture was stirred at room temperature for 1.5 hours. The reaction solution was added 1N-aqueous solution of hydrochloric acid under ice-cold conditions, and then a saturated aqueous solution of sodium hydrogen carbonate was added. The reaction solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (356 mg (yield 66%)) was obtained as a yellow solid.

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cb231cf4fbd748009a0805991cd0c2e6
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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