Methyl iodide → 4-methoxy-2,3-dihydro-1H-inden-1-one

HRID 255879

반응식

HRID 255879 반응식
CI.[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:13].[C:14](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:13]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5905474-Hydroxy-1-indanone

생성물 1

HCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Methyl iodide (69 ml) is added dropwise over a period of 15 minutes to a stirred mixture of 4-hydroxy-1-indanone (150 g) and anhydrous potassium carbonate (154 g) dissolved in DMF (1.5 liter) cooled to 0° C. under nitrogen. The reaction mixture is stirred at RT for 24 hours and partitioned between methylene chloride and water. The methylene chloride fraction is washed with water and 2% aqueous NaOH and dried over Na2SO4. The dried extract is filtered, concentrated in vacuo and the residue dissolved in hot methanol which upon cooling forms a precipitate. The precipitate is filtered and recrystallized from methanol yielding the methoxy product as a solid, M.P. 104°-106° C.

후처리

  1. custompartitioned between methylene chloride and water
  2. washThe methylene chloride fraction is washed with water and 2% aqueous NaOH
  3. dry with materialdried over Na2SO4
  4. extractionThe dried extract
  5. filtrationis filtered
  6. concentrationconcentrated in vacuo
  7. dissolutionthe residue dissolved in hot methanol which
  8. temperatureupon cooling forms a precipitate
  9. filtrationThe precipitate is filtered
  10. customrecrystallized from methanol yielding the methoxy product as a solid, M.P. 104°-106° C.

출처 및 근거

ORD 기록
ord-199a2fb1ff564d64b775b69167c04b6b
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04699906

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