Acetic Acid → HCID 89586109, compound

HRID 1747756Notes

Reaction equation

HRID 1747756 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9]CC)=O.[CH3:12][C:13]([CH3:15])=[O:14].CC(C)([O-])C.[K+].C(O)(=O)C>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:9])[CH2:12][C:13](=[O:14])[CH3:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 22456149Ethyl 3-bromofuran-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 89586109HCID 89586109, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of ethyl 3-bromofuran-2-carboxylate (16.2 g) and acetone (5.14 mL) in toluene (250 mL) was added potassium tert-butoxide (15.7 g) at 0° C. portionwise. The reaction mixture was stirred at room temperature for 2 hr, and acetic acid (8.01 mL) and water (250 mL) were added. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (10.9 g, enol/diketone=88/12).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-6d49d26bef7140a48a6da7c6f841c264
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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