Iodine → HCID 21281111, compound

HRID 414610Notes

Reaction equation

HRID 414610 reaction equation
[Mg].II.Br[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[O:10]([C:17]1[CH:18]=[C:19]([N:23]2[CH:27]=[CH:26][CH:25]=[C:24]2[CH:28]=[O:29])[CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH4+].[Cl-]>CCOCC>[OH:29][CH:28]([C:24]1[N:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:18]=2)[CH:27]=[CH:26][CH:25]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 5

HCID 807IodineHCID 80571-BromopentaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×HCID 14406222HCID 14406222, compound

Product 1

HCID 21281111HCID 21281111, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Magnesium turnings (2.4 g, 100 mmol) were activated with a crystal of iodine by heating under nitrogen the cooled magnesium and 6.1 g of 1-bromopentane (40 mmol, 99% purity) in 200 mL of ether. The reaction medium was heated to reflux and the reaction was self-sustaining. After 0.75 h the reaction was complete and the mixture was cooled to ice bath temperatures and 5 g of 1-(3-phenoxyphenyl)-pyrrole-2-aldehyde (19 mmol) in 25 mL of ether was added. The reaction was stirred for 1 h and poured into 500 ml of 1N NH4Cl solution. The product was extracted into ether and the ether was cross washed with 1 N NH4Cl solution. The etherate was separated, dried with MgSO4 and filtered, and the solvent was evaporated, yielding 6.35 g of crude product. The product was column chromatographed three times on silica gel (for dry column chromatography) and finally on Florisil eluting with ether acetate/hexane (1:40, v/v). After solvent removal, there was obtained 1.1 g of the final product. The product gave correct elemental analysis and spectral identification.

Workup

  1. temperatureThe reaction medium was heated
  2. temperatureto reflux
  3. additionwas added
  4. extractionThe product was extracted into ether
  5. washthe ether was cross washed with 1 N NH4Cl solution
  6. customThe etherate was separated
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customyielding 6.35 g of crude product
  11. customchromatographed three times on silica gel (for dry column chromatography)
  12. customAfter solvent removal

Sources & evidence

ORD record
ord-9206abde06534491ae3375bb1c261a03
Source dataset
uspto-grants-1988_12
Patent number
US04792568

Reaction notes

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