Iodine → HCID 22408172, compound

HRID 1654728Notes

Reaction equation

HRID 1654728 reaction equation
[Mg].II.[CH2:4]1[O:15][CH:7]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)[O:6][CH2:5]1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:26][CH3:27])[CH:25]=1)[CH:21]=[O:22].[Cl-].[NH4+]>O1CCCC1>[CH3:27][O:26][C:24]1[CH:23]=[C:20]([CH:19]=[C:18]([O:17][CH3:16])[CH:25]=1)[CH:21]([OH:22])[C:11]1[CH:12]=[CH:13][C:8]([CH:7]2[O:15][CH2:4][CH2:5][O:6]2)=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 817473,5-DimethoxybenzaldehydeHCID 27738422-(4-Bromophenyl)-1,3-dioxolaneHCID 5462224Magnesium2×

Product 1

HCID 22408172HCID 22408172, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of magnesium (0.9 g, 37 millimol) in tetrahydrofuran (30 ml) was added a small amount of iodine, and thereto was added a solution of p-bromobenzaldehyde ethylene acetal (8.0 g, 33 millimol) in tetrahydrofuran (10 ml) under nitrogen atmosphere. After a while, heat was generated, and magnesium was dissolved. After stirring for 1.5 hours as it was, the mixture was cooled with ice, and thereto was added at a breath 3,5-dimethoxybenzaldehyde (5 g, 30 millimol). After stirring for 2 hours as it was, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The residue was separated and purified by using a silica-gel column chromatography (ethyl acetate:n-hexane=1:2) to give the title compound (8.8 g, 27.7 millimol, 92%).

Workup

  1. temperatureAfter a while, heat
  2. temperaturethe mixture was cooled with ice
  3. stirringAfter stirring for 2 hours as it
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue was separated
  9. custompurified

Sources & evidence

ORD record
ord-876a5384c19b47408622a4c5e230bb93
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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