Water → 104501-20-4

HRID 649039Notes

Reaction equation

HRID 649039 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].[CH2:12](Br)[C:13]#[CH:14].O>O1CCCC1>[CH2:14]([N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7])[C:13]#[CH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromide2×HCID 24758Sodium hydrideHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 21278433104501-20-4

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

3.302 g of methyl 1H-pyrrole-2-carboxylate were dissolved in 40 ml of tetrahydrofuran and then, at 0° C., 1.422 g of sodium hydride in suspension at 50% in vaseline oil were added. The mixture stirred for 1 hour at 20° C. and a solution of 2 ml of propargyl bromide in 10 ml of tetrahydrofuran was introduced dropwise. The mixture was stirred for 1 hour at 50° C. and after having added 5 ml of propargyl bromide, the reaction mixture was poured into water. The mixture was extracted with methylene chloride and the extracts were concentrated to dryness by distilling under reduced pressure. The residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (9-1) to obtain 2.993 g of methyl 1-(2-propynyl)-1H-pyrrol-2-carboxylate.

Workup

  1. stirringThe mixture was stirred for 1 hour at 50° C.
  2. extractionThe mixture was extracted with methylene chloride
  3. concentrationthe extracts were concentrated to dryness
  4. distillationby distilling under reduced pressure
  5. customThe residue was chromatographed over silica
  6. washeluted with a mixture of hexane and ethyl acetate (9-1)

Sources & evidence

ORD record
ord-97cd30e86c224107bcb1cab3052f716c
Source dataset
uspto-grants-1988_04
Patent number
US04737513

Reaction notes

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