Sodium Iodide → HCID 68616983, compound

HRID 1158478Notes

Reaction equation

HRID 1158478 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([OH:13])[CH:6]=1)[CH3:2].[CH2:15]([O:17][CH2:18][CH2:19]Br)[CH3:16].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH2:16][CH2:15][O:17][CH2:18][CH3:19])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl ether2×HCID 15480330Ethyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 68616983HCID 68616983, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-hydroxy-4-methoxy-benzoic acid ethyl ester (1.60 g, 8.16 mmol), 2-bromoethyl ethyl ether (1.38 mL, 12.2 mmol) and anhydrous K2CO3 (1.69 g, 12.2 mmol) in MeCN (35 mL) is refluxed overnight. In order to complete the reaction, an additional aliquot of 2-bromoethyl ethyl ether (1.38 mL, 12.2 mmol) and a catalytic amount of NaI are added, and reflux is continued overnight. After cooling, the mixture is filtered and the filtrates are concentrated. The residue is taken up in CH2Cl2, the organic layer is washed with 0.5M NaOH and water, dried (Na2SO4) and concentrated. The title compound is obtained after flash chromatography (hexane/AcOEt 8:2) as colorless oil. MS: 269.0 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 4.92 min. 1H-NMR (CDCl3): δ 1.27 (m, 3H), 1.41 (m, 3H), 3.64 (m, 2H), 3.87 (m, 2H), 3.94 (s, 3H), 4.26 (m, 2H), 4.38 (m, 2H), 9.91 (dd, 1H), 7.63 (d, 1H), 7.72 (dd, 1H) ppm.

Workup

  1. temperatureis refluxed overnight
  2. customthe reaction
  3. temperaturereflux
  4. temperatureAfter cooling
  5. filtrationthe mixture is filtered
  6. concentrationthe filtrates are concentrated
  7. washthe organic layer is washed with 0.5M NaOH and water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e2bf7a1f456b4f8799e2029f7f791137
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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