Potassium Iodide → Ethyl 7-(Benzyloxy)chroman-2-carboxylate

HRID 989279Notes

Reaction equation

HRID 989279 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[CH2:25]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 11085381Ethyl 7-hydroxychromane-2-carboxylate

Product 1

HCID 11162736Ethyl 7-(Benzyloxy)chroman-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 7-hydroxy-chroman-2-carboxylate (6.1 g, 27.5 mmol), potassium carbonate (7.6 g, 55 mmol), potassium iodide (1.8 g, 11 mmol) and benzyl chloride (3.4 mL, 30 mmol) in acetone is heated at reflux for 16 hr under nitrogen, cooled, concentrated, diluted with water and extracted with EtOAc. The combined extracts are dried over MgSO4 and concentrated to afford the title compound as a straw-colored oil 8.58 g (100% yield), identified by NMR and mass spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hr under nitrogen
  3. temperaturecooled
  4. concentrationconcentrated
  5. additiondiluted with water
  6. extractionextracted with EtOAc
  7. dry with materialThe combined extracts are dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fe3e66d36ab04a229d785b251380ed8e
Source dataset
uspto-grants-2003_10
Patent number
US06638972B2

Reaction notes

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