Formaldehyde → 5-{[N-methyl-N-(2-propynyl)amino]methyl}-2-furanmethanol

HRID 1980658Notes

Reaction equation

HRID 1980658 reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:9][NH:10][CH2:11][C:12]#[CH:13].[CH2:14]=O.[OH-].[Na+]>>[CH3:9][N:10]([CH2:14][C:5]1[O:6][C:2]([CH2:1][OH:7])=[CH:3][CH:4]=1)[CH2:11][C:12]#[CH:13]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 7361Furfuryl AlcoholHCID 14798Sodium HydroxideHCID 22416630HCID 22416630, compound

Product 1

HCID 131029015-{[N-methyl-N-(2-propynyl)amino]methyl}-2-furanmethanol

Procedure

To furfuryl alcohol (2.49 g; 25.4 mmoles) which was cooled in an ice-water bath to 5° was added N-methylpropargylamine hydrochloride (4.0 g; 37.9 mmoles) and 40% formalin (3.13 ml; 41.7 mmoles), and the mixture stirred while allowed to reach ambient temperature. After 1 hour of stirring the solution was allowed to stand at ambient temperature for 41/2 days. The reaction mixture was poured into ice water, made strongly basic with 40% aqueous NaOH and extracted with five portions of methylene chloride. The combined organic phase was dried, filtered and evaporated under reduced pressure to give the product as an oil (quantitative yield). Vacuum distillation yielded the title compound, bp 102°-106°/0.3 mm Hg.

Workup

  1. customto reach ambient temperature
  2. stirringAfter 1 hour of stirring the solution
  3. customto stand at ambient temperature for 41
  4. custom2 days
  5. extractionextracted with five portions of methylene chloride
  6. customThe combined organic phase was dried
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7c7bae41ade74ca3a783c3fb412f2fe1
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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