Triacetoxyperiodinane → HCID 86674975, compound

HRID 468908Notes

Reaction equation

HRID 468908 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([Cl:10])[C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([Cl:10])[C:5]([CH:8]=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67975084HCID 67975084, compound

Product 1

HCID 86674975HCID 86674975, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5-bromo-3-chloro-4-methylpyridin-2-yl)methanol (255.6 mg; 1.081 mmol) in methylene chloride (8 mL; 124.8 mmol) was added Dess-Martin periodinane (0.5655 g; 1.293 mmol). The reaction mixture was stirred at room temperature for 17 hours. The reaction mixture was diluted with additional dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (24 g silica, solvent gradient: 0-80% ethyl acetate in dichloromethane) to yield 226.5 mg (89%) of the title compound. LCMS (ESI): M+H=234.2; 1H NMR (400 MHz, CDCl3) δ 10.30 (s, 1H), 8.75 (s, 1H), 2.63 (s, 3H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified via flash chromatography on silica gel (24 g silica, solvent gradient: 0-80% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-ec60aaea863446ec83c71549ce11dc3f
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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