Iodoethane → HCID 178466714, compound

HRID 1990835Notes

Reaction equation

HRID 1990835 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10](C)([O-])C.[Na+].C(I)C>CO>[CH2:9]([O:8][C:7]1[C:2]([OH:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[CH3:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 23676156Sodium t-butoxideHCID 178516237HCID 178516237, compound

Product 1

HCID 178466714HCID 178466714, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,3-dihydroxypyridine (5.0 g, 45.0 mmol, 1.0 equiv) and sodium tert-butoxide (4.33 g, 45.0 mmol, 1.0 equiv) in methanol (25 mL) was added ethyl iodide (5.21 mL, 7.72 g, 49.5 mmol, 1.1 equiv) and the reaction mixture heated to 100° C. under microwave irradiation for 20 min. The solvent was removed and the reaction product dissolved in dichloromethane (50 mL), the obtained suspension filtered and the organic phase concentrated by evaporation under reduced pressure. The crude material was purified by column chromatography on silica eluting with dichloromethane/methanol (9:1) yielding 3.0 g (41%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 3H), 4.05 (q, J=7.0 Hz, 2H), 6.20 (t, J=7.1 Hz, 1H), 6.76 (dd, J=7.4 Hz, J=1.3 Hz, 1H), 7.05 (dd, J=6.5 Hz, J=1.3 Hz, 1H), 13.36 (br s, 1H).

Workup

  1. customThe solvent was removed
  2. dissolutionthe reaction product dissolved in dichloromethane (50 mL)
  3. filtrationthe obtained suspension filtered
  4. concentrationthe organic phase concentrated by evaporation under reduced pressure
  5. customThe crude material was purified by column chromatography on silica eluting with dichloromethane/methanol (9:1)

Sources & evidence

ORD record
ord-691eca8446ee4df382146d54ccea31db
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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