Propargyl bromide → HCID 13605018, compound

HRID 649030Notes

Reaction equation

HRID 649030 reaction equation
[N+:1]([C:4]1[C:8]([CH:9]=[O:10])=[CH:7][NH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:13](Br)[C:14]#[CH:15]>O1CCCC1>[N+:1]([C:4]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]([CH2:15][C:14]#[CH:13])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 21278472HCID 21278472, compound

Product 1

HCID 13605018HCID 13605018, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

826 mg of 3-nitro-1H-pyrrole-4-carboxaldehyde [prepared by the process in Bull. Soc. Chim. p. 283-29 (1972)] were poured into 40 ml of tetrahydrofuran and then, at +5° C., 280 mg of sodium hydride as 50% in oil were added. After leaving the temperature at 20° C. for one hour, 1.19 g of propargyl bromide were added. The mixture was stirred for 18 hours at 20° C. and then was filtered and concentrated. The residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (1-1) to obtain 800 mg of 3-nitro-1-(2-propynyl) 1H-pyrrol-4-carboxaldehyde melting at 120° C.

Workup

  1. customAfter leaving the temperature at 20° C. for one hour
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customThe residue was chromatographed over silica
  5. washeluted with a mixture of hexane and ethyl acetate (1-1)

Sources & evidence

ORD record
ord-777751b9176f46d2a23caef565dcfdcd
Source dataset
uspto-grants-1988_04
Patent number
US04737513

Reaction notes

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