Iodine → HCID 131719562, compound

HRID 744179Notes

Reaction equation

HRID 744179 reaction equation
II.[C:3]1([C:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([O:18][SiH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]2[N:15]=[C:14]([CH:16]=[O:17])[CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[K].[CH3:31][OH:32]>>[CH3:31][O:32][C:16]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([C:9]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:18][SiH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[N:15]=1)=[O:17]

Participants

5

Reactant 4

HCID 807Iodine2×HCID 887Methanol2×HCID 5462222PotassiumHCID 1317195606-[Tert-butylsilyloxy(diphenyl)methyl]pyridine-2-carbaldehyde

Product 1

HCID 131719562HCID 131719562, compound

Procedure

A solution of 8.15 g of iodine in 148 ml of methanol is instilled in a solution of 18.29 g of 6-(diphenyl-tert-butylsilyloxymethyl)-2-pyridinecarbaldehyde and 7.22 g of potassium hydroxidelin 593 ml of methanol at 0° C. under nitrogen. After 1 hour of stirring, iodine solution was again.added and subsequently stirred, and this was also repeated until a complete reaction was discernible in the thin layer. The reaction mixture is concentrated by evaporation in a vacuum up to about 60 ml, mixed with 100 ml of semiconcentrated sodium chloride solution and extracted four times with ether. The combined organic phases are washed once with 60 ml of saturated sodium thiosulfate solution, semiconcentrated sodium. chloride solution, dried on sodium sulfate and after filtration, concentrated by evaporation in a vacuum. 19.4 g of the title compound is obtained, which is further used without further purification.

Workup

  1. stirringsubsequently stirred
  2. customthis was also repeated until a complete reaction
  3. concentrationThe reaction mixture is concentrated by evaporation in a vacuum up to about 60 ml
  4. additionmixed with 100 ml of semiconcentrated sodium chloride solution
  5. extractionextracted four times with ether
  6. washThe combined organic phases are washed once with 60 ml of saturated sodium thiosulfate solution, semiconcentrated sodium
  7. dry with materialchloride solution, dried on sodium sulfate
  8. filtrationafter filtration
  9. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-6cf968dac428413b9a699f7abe3123e4
Source dataset
uspto-grants-1996_09
Patent number
US05559134

Reaction notes

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