Triacetoxyperiodinane → HCID 64996782, compound

HRID 1672819Notes

Reaction equation

HRID 1672819 reaction equation
[OH:1][CH:2]([CH3:14])[CH2:3][NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([I:12])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>ClCCl>[I:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:5]([NH:4][CH2:3][C:2](=[O:1])[CH3:14])=[O:13]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 43391001HCID 43391001, compound

Product 1

HCID 64996782HCID 64996782, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(2-Hydroxypropyl)-3-iodobenzamide (1.09 g, 3.57 mmol) obtained in Step 1 was dissolved in dichloromethane (40 mL), cooled to 0° C., and stirred at room temperature for 1 hour after adding Dess-Martin periodinane (1.82 g, 4.28 mmol). Thereafter, a saturated aqueous sodium bicarbonate solution was added to the mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The residue obtained upon concentration was purified by silica gel column chromatography to give 3-iodo-N-(2-oxopropyl)benzamide (1.01 g, 93%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe residue obtained upon concentration
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cc10d2c0f106423bb1944444c1d14fde
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…