Hydrochloric Acid → HCID 68320241, compound

HRID 332588Notes

Reaction equation

HRID 332588 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7](/[CH:10]=[C:11](/[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])\[CH3:12])=[CH:8][CH:9]=1)=[O:4].[OH-].[Li+].Cl>CO>[C:16]([O:15][C:13](/[C:11](/[CH3:12])=[CH:10]/[C:7]1[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 70869509HCID 70869509, compound

Product 1

HCID 68320241HCID 68320241, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-[(1E)-2-(tert-butoxycarbonyl)-prop-1-en-1-yl]furan-2-carboxylic acid methyl ester (1.11 g, 4.17 mmol) obtained in step 1 was dissolved in methanol (7.65 mL), 1N aqueous lithium hydroxide solution (6.25 mL, 6.25 mmol) was added, and the mixture was stirred at room temperature for 100 minutes. 1N aqueous hydrochloric acid solution (6.25 mL) was added, the mixture was stirred for 10 minutes, and the solvent was evaporated under reduced pressure. To the residue were added ethyl acetate and 0.5N aqueous hydrochloric acid solution, the organic layer was extracted, and the aqueous layer was extracted three times with ethyl acetate. The organic layers were collected, washed with saturated brine and dried by dehydration with sodium sulfate. The solvent of the filtrate after filtration was evaporated under reduced pressure to give the title compound.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the residue were added ethyl acetate and 0.5N aqueous hydrochloric acid solution
  4. extractionthe organic layer was extracted
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. customThe organic layers were collected
  7. washwashed with saturated brine
  8. dry with materialdried by dehydration with sodium sulfate
  9. filtrationThe solvent of the filtrate after filtration
  10. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-5228950a952348088d5c6aeaef1bfb67
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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