Hydrochloric Acid → 5-(1-Hydroxy-2-methylprop-2-enyl)furan-2-carboxylic acid benzyl ester

HRID 517341

Reaction equation

HRID 517341 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([Mg]Br)[CH:19]=[CH2:20].Cl>O1CCCC1>[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([CH:16]([OH:17])[C:19]([CH3:20])=[CH2:18])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 600347885-Formyl-2-furancarboxylic acid benzyl esterHCID 178455850HCID 178455850, compound

Product 1

HCID 866733225-(1-Hydroxy-2-methylprop-2-enyl)furan-2-carboxylic acid benzyl esterYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Formyl-2-furancarboxylic acid benzyl ester (300 mg, 1.30 mmol) was dissolved in tetrahydrofuran (12 mL), 2-propenylmagnesium bromide (0.5 mol/L tetrahydrofuran solution, 2.6 mL, 1.3 mmol) was added at −78° C., and the mixture was stirred for 15 minutes. 1N Hydrochloric acid was added to the reaction mixture, the mixture was heated to room temperature and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30) to give the title compound (332 mg, 1.23 mmol, 94%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-04b6908042264acf902e11a911eeffdb
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Linked notes

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