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

HRID 264541

반응식

HRID 264541 반응식
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]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 1061PhosphateHCID 25517Ammonium ChlorideHCID 677142662-(2,2-dimethoxy-1-ethyl)-5-methoxy-1-tetralone N,N-dimethylhydrazone

생성물 1

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

시약·촉매·용매 2

HCID 61482Cupric chloride dihydrate촉매HCID 8028Tetrahydrofuran용매

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-1811e1398c7448c0b99f32f53ed03a7f
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646173

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