Triacetoxyperiodinane → N-(4-Chloro-3-formylbenzyl)-N-methylacetamide

HRID 561791Notes

Reaction equation

HRID 561791 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]([CH3:11])[C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH2:14][OH:15].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]([CH3:11])[C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH:14]=[O:15]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66761682N-[4-Chloro-3-(hydroxymethyl)benzyl]-N-methylacetamide

Product 1

HCID 86635912N-(4-Chloro-3-formylbenzyl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[4-chloro-3-(hydroxymethyl)benzyl]-N-methylacetamide from the previous step (1 eq.) in CH2Cl2 (0.8 M) was added Dess-Martin periodinane (1.2 eq.) portionwise. The resulting suspension was stirred at RT for 3 h. The reaction was quenched with MeOH and H2O. The organic layer was separated and the aqueous layer was back-extracted with EtOAc. The combined organic extracts were washed sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. customThe reaction was quenched with MeOH and H2O
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back-extracted with EtOAc
  4. washThe combined organic extracts were washed sat. aq. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customConcentration of the filtrate in vacuo afforded a pale yellow oil
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-0d3255f9dfb34e39bb6660e23d7106e8
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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