Iodine → HCID 66771403, compound

HRID 1697760Notes

Reaction equation

HRID 1697760 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:11][CH2:10][O:9][C:8]2=[O:12])=[CH:4][CH:3]=1.II.[CH3:17][OH:18]>>[CH3:17][O:18][C:8](=[O:12])[CH:7]([O:6][C:5]1[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:11][CH2:10][OH:9]

Participants

4

Reactant 3

HCID 807IodineHCID 887MethanolHCID 19261280HCID 19261280, compound

Product 1

HCID 66771403HCID 66771403, compoundYield 33%

Procedure

3-(4-chlorophenoxy)dihydrofuran-2(3H)-one, (Example 473a), 1.136 g), iodine (30.0 mg) and methanol (28.9 mL) were stirred at 65° C. for 24 hr. The reaction mixture was concentrated in vacuo. Exces of iodine was eliminante by adding an aqueous solution of sodium sulfite (10% w/w, 15 mL). The mixture was extracted with ethyl acetate. The organic layers were washed with brine (10 mL), dried over sodium sulfate and filtered. The crude mixture was concentrated to dryness and purified by chromatography on silica gel to yield the title compound as a colorless oil (433 mg; 33%). MS (ESI): m/z=244 [M]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionby adding an aqueous solution of sodium sulfite (10% w/w, 15 mL)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe crude mixture was concentrated to dryness
  8. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-cac97db9c0294a4fb785ce9f8f0462b3
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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