Dimethyl Sulfate → HCID 22397029, compound

HRID 1070454Notes

Reaction equation

HRID 1070454 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[C:8]([Br:17])[C:7]=1O)=[O:5])[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].S([O:30][CH3:31])(OC)(=O)=O>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][CH3:19])=[C:8]([Br:17])[C:7]=1[O:30][CH3:31])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 22397020HCID 22397020, compound

Product 1

HCID 22397029HCID 22397029, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl-3-bromo-2,4-dihydroxy-1-naphthoate (5.8 g, 18.6 mmol) in acetone (93 mL) was added potassium carbonate (6.43 g, 46.6 mmol) and dimethyl sulfate (4.4 mL, 46.6 mmol). The mixture was heated under reflux overnight and solvent was removed in vacuo. Water and EtOAc was added and the organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography (eluting with 3-5% EtOAc/hexane) to give the product (6.23 g, 99% yield) as a light yellow oil. 1H NMR (CDCl3) δ 8.13 (d, 1H), 7.83 (d, 1H), 7.62-7.48 (m, 2H), 4.54 (q, 2H), 4.02 (s, 3H), 4.00 (s, 3H), 1.46 (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customsolvent was removed in vacuo
  4. additionWater and EtOAc was added
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography (eluting with 3-5% EtOAc/hexane)

Sources & evidence

ORD record
ord-496c4559f7d9417e82d7140c490ebe8d
Source dataset
uspto-grants-2005_06
Patent number
US06903092B2

Reaction notes

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