Triacetoxyperiodinane → HCID 58191768, compound

HRID 1034615Notes

Reaction equation

HRID 1034615 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:16])[CH2:9][CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[C:5]([F:17])=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:16])[CH2:9][CH2:10][CH:11]([O:12][CH3:13])[O:14][CH3:15])[C:5]([F:17])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58191784HCID 58191784, compound

Product 1

HCID 58191768HCID 58191768, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The suspension of 1-(2-chloro-5-fluoro-pyridin-4-yl)-4,4-dimethoxy-butan-1-ol (0.80 g, 3.03 mmol) and Dess-Martin reagent (1.54 g, 3.64 mmol) in DCM (20 mL) is stirred at room temperature for 3 hours. The precipitate is filtered. Water is added to the filtrate and extracted with DCM. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by chromatography (EtOAc/hexane: 5%˜20%) to give 1-(2-chloro-5-fluoro-pyridin-4-yl)-4,4-dimethoxy-butan-1-one (0.71 g, 89%). M/Z=262.10 [M+1]

Workup

  1. filtrationThe precipitate is filtered
  2. additionWater is added to the filtrate
  3. extractionextracted with DCM
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. customThe crude product is purified by chromatography (EtOAc/hexane: 5%˜20%)

Sources & evidence

ORD record
ord-2ff769250a554df08026cba408771c1d
Source dataset
uspto-grants-2013_10
Patent number
US08546336B2

Reaction notes

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