Ammonia → 2-(2-Oxoethyl)-5-methoxy-1-tetralone

HRID 264541

Reaction equation

HRID 264541 reaction equation
CN(C)N=[C:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]1[CH2:16][CH:17]([O:20]C)OC.P([O-])([O-])([O-])=[O:24].[Cl-].[NH4+].N>C1COCC1.O.O.[Cu](Cl)Cl>[O:20]=[CH:17][CH2:16][CH:5]1[CH2:6][CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[C:4]1=[O:24]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1061PhosphateHCID 25517Ammonium ChlorideHCID 67714266HCID 67714266, compound

Product 1

HCID 190363722-(2-Oxoethyl)-5-methoxy-1-tetraloneYield 80%

Reagents, catalysts & solvents 2

HCID 61482Cupric chloride dihydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

280 mg of 2-(2,2-dimethoxy-1-ethyl)-5-methoxy-1-tetralone N,N-dimethylhydrazone were dissolved in 12.5 ml of THF and added to 5 ml of phosphate buffer (prepared from 2 ml of 1/15M potassium dihydrogen phosphate and 3 ml of 1/15M disodium hydrogen phosphate) as well as 156 mg of copper (II) chloride dihydrate. After stirring at room temperature for 3.5 hours, the reaction had finished. The mixture was treated with 10 ml of 20% ammonium chloride solution and 0.8 ml of conc ammonia. Then, the mixture was extracted several times with ethyl acetate, dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on silica gel firstly with toluene, then with toluene/ethyl acetate 9:1. 180 mg (80%) of 2-(2-oxoethyl)-5-methoxy-1-tetralone were obtained as a yellowish oil (Rf=0.31, silica gel (toluene/ethyl acetate 9:1)).

Workup

  1. extractionThen, the mixture was extracted several times with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel firstly with toluene

Sources & evidence

ORD record
ord-1811e1398c7448c0b99f32f53ed03a7f
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Linked notes

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