1,4-Dibromobutane → HCID 117874403, compound

HRID 2272866Notes

Reaction equation

HRID 2272866 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([O:10][CH3:11])=[O:9].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16]Br>C1COCC1>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 117874403HCID 117874403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6.7 g (241.7 mmol) of NaH (60%) in 400 mL of anhydrous THF at 0° C. there are added 20 g (161.13 mmol) of methyl 1H-pyrrole-2-carboxylate (see Tetrahedron 2008, 64, 7745). The whole is subsequently stirred at ambient temperature for one hour. Then, there are added 95 mL of 1,4-dibromobutane. After the addition, the reaction mixture is heated at reflux for 12 hours. The precipitate obtained is filtered off and then washed with THF. The filtrate is subsequently concentrated to dryness. The compound is then isolated by chromatography over silica gel (cyclohexane/ethyl acetate gradient: 0 to 20%) in the form of an oil.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture is heated
  3. temperatureat reflux for 12 hours
  4. customThe precipitate obtained
  5. filtrationis filtered off
  6. washwashed with THF
  7. concentrationThe filtrate is subsequently concentrated to dryness
  8. customThe compound is then isolated by chromatography over silica gel (cyclohexane/ethyl acetate gradient: 0 to 20%) in the form of an oil

Sources & evidence

ORD record
ord-46247c0e2abc4ffcafd38e60cdd2a1cb
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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