Acetone → 5-(4-Bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone

HRID 1193043Notes

Reaction equation

HRID 1193043 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)O)=[C:4]([CH2:15][CH3:16])[CH:3]=1.CC(C)=[O:19]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:11])[CH:13]=[CH:14][CH:10]2[OH:19])=[C:4]([CH2:15][CH3:16])[CH:3]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 58070821(4-Bromo-2-ethylphenyl)furan-2-yl-methanol

Product 1

HCID 580708725-(4-Bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (4-bromo-2-ethylphenyl)furan-2-yl-methanol (13.6 g, 0.039 mol) in acetone (300 ml) and water (30 ml) at 55° C. is added polyphosphoric acid (5.0 g, 0.05 mol). After stirring at this temperature for 20 hours the reaction mixture is cooled to room temperature then concentrated in vacuo. The crude product is then partitioned between ethyl acetate (200 ml) and water (200 ml), and the organic phase is separated. After drying over anhydrous magnesium sulfate, all solvents are removed and the crude product is purified by flash column chromatography (1:1 ethyl acetate/hexane) to afford 5-(4-bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone as a brown gum.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude product is then partitioned between ethyl acetate (200 ml) and water (200 ml)
  3. customthe organic phase is separated
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customall solvents are removed
  6. customthe crude product is purified by flash column chromatography (1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c0571d27379b4395afa8217af1f9509a
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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