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

HRID 1702338Notes

Reaction equation

HRID 1702338 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-2771a65f088c413786c57f67e9c01394
Source dataset
uspto-grants-1983_04
Patent number
US04380639

Reaction notes

Loading…