Iodine → HCID 69101330, compound

HRID 2222570Notes

Reaction equation

HRID 2222570 reaction equation
[Mg].II.Br[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[C:12]1(=[O:32])[N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=O)[C:15](=[O:27])[C:14]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:13]12.CC[O:35]CC>>[OH:35][CH:5]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:12](=[O:32])[C:13]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:14]2[C:15]1=[O:27]

Participants

6

Reactant 5

HCID 807IodineHCID 3283Diethyl EtherHCID 6427994-(Bromomethyl)pyridineHCID 5462224MagnesiumHCID 59709149HCID 59709149, compound

Product 1

HCID 69101330HCID 69101330, compound

Procedure

Magnesium (1.2 equiv.) is stirred in anhydrous ether under a nitrogen atmosphere and a catalytic amount of iodine is added. The mixture is heated to reflux and 4-bromomethylpyridine (1 equiv.) is added. The reaction is stirred until formation of the Grignard reagent is complete and 9-phthalimidononanal (1.5 equiv.) is added. The reaction mixture is stirred until completion, quenched with ammonium chloride, extracted with brine and concentrated in vacuo. The crude product is purified by silica gel chromatography to give 1-hydroxy-1-(4-pyridinyl)-10-phthalimidodecane.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customquenched with ammonium chloride
  4. extractionextracted with brine
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-7d640db741b54ca9b38d8f519d78f616
Source dataset
uspto-grants-2008_05
Patent number
US07371852B2

Reaction notes

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