Triacetoxyperiodinane → HCID 86674975, compound

HRID 1502425Notes

Reaction equation

HRID 1502425 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-3d412759aa5c4e5a8fcb005d07940950
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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