Sodium Hydroxide → (Furo[3,2-c]pyridin-6-yl)methanol

HRID 1383003Notes

Reaction equation

HRID 1383003 reaction equation
[OH2:1].[CH3:2][C:3]1[N+:8]([O-])=[CH:7][C:6]2[CH:10]=[CH:11][O:12][C:5]=2[CH:4]=1.[OH-].[Na+]>C(OC(=O)C)(=O)C.Cl>[OH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]2[CH:10]=[CH:11][O:12][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21273331HCID 21273331, compound

Product 1

HCID 14005234(Furo[3,2-c]pyridin-6-yl)methanolYield 64%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-methylfuro[3,2-c]pyridine-N-oxide monohydrate (19.85 g, 0.119 mol) in acetic anhydride (30 mL) was heated at 100° C. for one half hour. Then the reaction mixture was diluted with 20% hydrochloric acid (100 mL) and heating was continued for one hour. The solution was cooled and made basic with sodium hydroxide solution. The product was extracted into chloroform, dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated. The residue was triturated with cool benzene and the crystalline product collected by filtration to give 11.36 g (64% yield), mp: 72°-74° C.

Workup

  1. temperatureheating
  2. temperatureThe solution was cooled
  3. extractionThe product was extracted into chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered through a pad of charcoal
  6. customevaporated
  7. customThe residue was triturated with cool benzene
  8. filtrationthe crystalline product collected by filtration
  9. customto give 11.36 g (64% yield), mp: 72°-74° C.

Sources & evidence

ORD record
ord-a409d72270784fcf98f40e0d728af78f
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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