Triacetoxyperiodinane → HCID 58111889, compound

HRID 1038647Notes

Reaction equation

HRID 1038647 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:13])[CH2:9][CH2:10][CH:11]=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58111872HCID 58111872, compound

Product 1

HCID 58111889HCID 58111889, compoundYield 124.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(5-bromo-pyridin-3-yl)-4-hydroxy-butan-1-one (1) (5.0 g, 20.5 mmole) in 90 mL of CH2Cl2 at 25° C., is added a solution of Dess-Martin periodinane (9.6 g, 22.5 mmole) in 70 mL of CH2Cl2 slowly. After stirring at 25° C. for 20 minutes, the reaction mixture is diluted with 200 mL of ether (a lot of white precipitates came out of the solution) and cooled by dry-ice-acetone bath. The solid is filtered out and discarded. The filtrate is concentrated. The residue is diluted with 100 mL of ether and cooled by dry-ice-acetone bath and precipitates was removed by filtration. The filtrate is concentrated to give 6.2 g of 4-(5-Bromo-pyridin-3-yl)-4-oxo-butyraldehyde (2) as a pale brown oil which turned to a pale brown solid after cooled to 0° C., without further purification for next step reaction.

Workup

  1. customof white precipitates
  2. temperaturecooled by dry-ice-acetone bath
  3. filtrationThe solid is filtered out and
  4. concentrationThe filtrate is concentrated
  5. additionThe residue is diluted with 100 mL of ether
  6. temperaturecooled by dry-ice-acetone bath
  7. customprecipitates
  8. customwas removed by filtration
  9. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-95d6c79abecc45cfa66bf19fd4dee1a7
Source dataset
uspto-grants-2013_10
Patent number
US08552003B2

Reaction notes

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