Triethylamine → (+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone oxime

HRID 2307108Notes

Reaction equation

HRID 2307108 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)CC)C.[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH2:22][O:23][CH3:24])[CH:18]=[CH:17][C:16]=1[CH:25]1[CH2:30][CH2:29][CH2:28][C:27](=O)[CH2:26]1>C(O)C>[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH2:22][O:23][CH3:24])[CH:18]=[CH:17][C:16]=1[CH:25]1[CH2:30][CH2:29][CH2:28][C:27](=[N:2][OH:3])[CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 22337753(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone

Product 1

HCID 86586318(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone oximeYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (71 mg), triethylamine (0.17 ml) and (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexanone (200 mg) were heated under reflux in ethanol (8 ml). After 0.75 hr, the reaction mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish the title compound as a pale yellow oil (197 mg, 94%); m/z (ES+) 310 (M+H)+.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v)

Sources & evidence

ORD record
ord-8dbe6d1e0bf1491e9c6d8b9ec70decdc
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

Loading…