Ethyl Acetate → 1-(2-chloro-5-nitropyridin-4-yl)ethanone

HRID 1028044Notes

Reaction equation

HRID 1028044 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:10])[CH3:9])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)(=O)C>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 58387595HCID 58387595, compound

Product 1

HCID 583875681-(2-chloro-5-nitropyridin-4-yl)ethanoneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chloro-5-nitropyridin-4-yl)ethanol (1.0 equiv.) in dichloromethane (0.1 M) was added Dess-Martin periodinane (1.8 eq.) and the solution was stirred for 16 hours. The solution was poured into ethyl acetate (800 mL), was washed with 1:1 10% Na2S2O3/NaHCO3(sat.) (4×), with NaCl(sat.), dried over MgSO4, filtered and concentrated yielding 1-(2-chloro-5-nitropyridin-4-yl)ethanone (96%) as a yellow solid. LCMS (m/z): 201.0 (MH+); LC Rt=2.80 min. 1H NMR (CDCl3): δ 9.18 (s, 1H), 7.36 (s, 1H), 2.60 (s, 3H).

Workup

  1. washwas washed with 1:1 10% Na2S2O3/NaHCO3(sat.) (4×), with NaCl(sat.)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-06315a428c6e4d13a27a5029b75b1435
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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