Triethylamine → (+/-)-3-(2,4-Dihydroxyphenyl)cyclopentanone Oxime

HRID 2307165Notes

Reaction equation

HRID 2307165 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:13][CH2:12][C:11](=O)[CH2:10]1.Cl.[NH2:16][OH:17].C(N(CC)CC)C>CCO>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:13][CH2:12][C:11](=[N:16][OH:17])[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 22337821(+/-)-3-(2,4-Dihydroxyphenyl)cyclopentanone

Product 1

HCID 86586325(+/-)-3-(2,4-Dihydroxyphenyl)cyclopentanone Oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-3-(2,4-Dihydroxyphenyl)cyclopentanone (5 mg), hydroxylamine hydrochloride (2.7 mg) and triethylamine (5.4 uM) were heated in EtOH (4 ml) under reflux for 3 hr. The reaction mixture was partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous phase was extracted with ethyl acetate (10 ml), and the combined organic phases were washed with brine (10 ml), dried over magnesium sulfate, and concentrated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 4:1 v/v) to furnish the title compound as a white solid and a mixture of isomers (3.8 mg, 71%). δH (d4-MeOH) 1.80-1.93 (1H, overlapping m), 2.05-2.20 (0.5H, m), 2.39-2.55 (3H, overlapping m), 2.68-2.74 (1H, overlapping m), 2.94 (0.5H, br dd), 6.26-6.33 (2H, overlapping m), 6.94 (0.5H, d), 6.96 (0.5H, d); m/z (ES−) 266 ((M+60)−1)−.

Workup

  1. temperatureunder reflux for 3 hr
  2. customThe reaction mixture was partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (10 ml)
  4. washthe combined organic phases were washed with brine (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 4:1 v/v)

Sources & evidence

ORD record
ord-0d4fe1b1121d4d6aabd94ddd0c67f235
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

Loading…