3-Furaldehyde → HCID 19047560, compound

HRID 742483Notes

Reaction equation

HRID 742483 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[C:8]([Mg]Br)#[CH:9].[Cl-].[NH4+]>C1COCC1>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([OH:7])[C:8]#[CH:9])=[CH:2]1

Participants

5

Reactant 3

HCID 103513-FuraldehydeHCID 25517Ammonium ChlorideHCID 178418486HCID 178418486, compound

Product 1

HCID 19047560HCID 19047560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-furaldehyde (25.0g, 0.26 mol) in THF (250 mL) at 78° C. was added ethynylmagnesium bromide (572 mL, 0.286, 0.5M THF) at the rate of 10 mL per min. The mixture was slowly warmed to room temperature, stirred for 1 h and then poured into a cooled ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was distilled at 50°-55° C. and 0.24 mm Hg to afford 1-(3-furyl)-1-hydroxy-2-propyne.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. distillationThe residue was distilled at 50°-55° C.

Sources & evidence

ORD record
ord-d9128801d1614b7d939147beb871031e
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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