2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 2-(2,2-dimethoxy-1-ethyl)-5-methoxy-1-tetralone N,N-dimethylhydrazone

HRID 264540

반응식

HRID 264540 반응식
[CH3:1][N:2]([CH3:16])[N:3]=[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][CH2:5]1.CN1C(=O)N(C)CCC1.C([Li])CCC.[CH3:31][O:32][CH:33]([O:36][CH3:37])[CH2:34]Br>C1COCC1.CCCCCC.O>[CH3:1][N:2]([CH3:16])[N:3]=[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[CH2:34][CH:33]([O:36][CH3:37])[O:32][CH3:31]

참가 물질

8

반응물 4

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 816722-Bromo-1,1-dimethoxyethaneHCID 290941HCID 290941, 화합물HCID 178418339Butyllithium

생성물 1

HCID 677142662-(2,2-dimethoxy-1-ethyl)-5-methoxy-1-tetralone N,N-dimethylhydrazone수율 37%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

3.12 g of 5-methoxy-1-tetralone N,N-dimethylhydrazone and 4.15 ml of DMPU were dissolved in 70 ml of absolute THF under argon and cooled to -75°. 10.7 ml of a 1.6M solution of n-butyllithium in hexane were added dropwise. The mixture was stirred at -75° for 1 hour and thereupon treated slowly with 2.0 ml of bromoacetaldehyde dimethyl acetal. The mixture was left to warm to room temperature and stirred for 26 hours. 20 ml of water were added at about 0° and the mixture was extracted three times with ethyl acetate. After drying over sodium sulfate, the mixture was filtered, evaporated and the residue was chromatographed on silica gel with toluene, then with toluene/ethyl acetate 9:1. 1.62 g (37%) of 2-(2,2-dimethoxy-1-ethyl)-5-methoxy-1-tetralone N,N-dimethylhydrazone were obtained as an oil.

후처리

  1. temperaturecooled to -75°
  2. waitThe mixture was left
  3. stirringstirred for 26 hours
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. dry with materialAfter drying over sodium sulfate
  6. filtrationthe mixture was filtered
  7. customevaporated
  8. customthe residue was chromatographed on silica gel with toluene

출처 및 근거

ORD 기록
ord-f0ae9af437a8485ebac27d545625552a
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646173

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