Methanol → HCID 58875428, compound

HRID 2377123Notes

Reaction equation

HRID 2377123 reaction equation
[C:1]([C:4]1[O:8][C:7]([C:9](O)([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH3:15]O>>[CH3:15][O:3][C:1]([C:4]1[O:8][C:7](/[C:9](/[CH2:12][CH3:13])=[CH:10]/[CH3:11])=[CH:6][CH:5]=1)=[O:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 58875427HCID 58875427, compound

Product 1

HCID 58875428HCID 58875428, compound

Procedure

3-(5-Carboxy-2-furanyl)pentan-3-ol (200 mg, 1.1 mmol) is dissolved in methanol (20 mL). HCl (g) is bubbled through the solution for 30 seconds. The reaction is stirred for 20 minutes at room temperature with no reaction. The solution is heated to 60° C. for 2 hours. The solution is concentrated and water is added followed by solid NaHCO3 until the pH was basic. Ethyl acetate is added and the solution is extracted. The organic layer is washed with water, dried over MgSO4 and filtered. The filtrate is concentrated to 213 mg of an orange oil which is used as is.

Workup

  1. customHCl (g) is bubbled through the solution for 30 seconds
  2. temperatureThe solution is heated to 60° C. for 2 hours
  3. concentrationThe solution is concentrated
  4. additionwater is added
  5. additionEthyl acetate is added
  6. extractionthe solution is extracted
  7. washThe organic layer is washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated to 213 mg of an orange oil which

Sources & evidence

ORD record
ord-a99eaad7fe49464faf33a1bf5ab0c728
Source dataset
uspto-grants-2008_12
Patent number
US07468449B2

Reaction notes

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