Toluene → 8-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1h)-one

HRID 61859노트

반응식

HRID 61859 반응식
C[C:2](C)([O-:4])C.[Na+].C[O:8][C:9]1[CH:10]=CC=[C:13]2[C:18]=1[CH2:17]C(=O)CC2.CI.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:2][O:4][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[C:18]([CH3:13])([CH3:17])[C:9](=[O:8])[CH2:10][CH2:28]2

참가 물질

5

반응물 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 41360218-Methoxy-2-tetraloneHCID 23676156Sodium t-butoxide

생성물 1

HCID 2637288-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1h)-one

반응 조건

온도
15 °C

실험 절차

To the toluene suspension of sodium t-butoxide (700 mg, 2.5 eq.), 8-methoxy-3,4-dihydro-1H-naphthalen-2-one (Compound W1, 500 mg, 2.9 mmol) was added dropwise at 0° C. After 15 minutes, the solution turned into blackish green color. The mixture solution was added dropwise with methyl iodide (1.03 g, 2.5 eq.) and stirred at 15° C. overnight. Brown solid precipitated. The reaction solution was added to saturated aqueous solution of ammonium chloride/diethyl ether under stirring and cooling. After that, the solution was extracted with diethyl ether, and dried over sodium sulfate. After removing the solvent under reduced pressure, the resulting residues were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain 8-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (350 mg).

후처리

  1. additionwas added dropwise at 0° C
  2. customBrown solid precipitated
  3. additionThe reaction solution was added to saturated aqueous solution of ammonium chloride/diethyl ether
  4. stirringunder stirring
  5. temperaturecooling
  6. extractionAfter that, the solution was extracted with diethyl ether
  7. dry with materialdried over sodium sulfate
  8. customAfter removing the solvent under reduced pressure
  9. customthe resulting residues were purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-5330bd5db0564582a08ee64d52b65d0a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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