Hydrochloric Acid → 1,3-Dicyclopropylpropane-1,3-dione

HRID 31153

반응식

HRID 31153 반응식
CO[C:3]([CH:5]1[CH2:7][CH2:6]1)=[O:4].[CH:8]1([C:11](=[O:13])[CH3:12])[CH2:10][CH2:9]1.C[O-].[Na+].Cl>CS(C)=O.C1(C)C=CC=CC=1>[CH:5]1([C:3](=[O:4])[CH2:12][C:11]([CH:8]2[CH2:10][CH2:9]2)=[O:13])[CH2:6][CH2:7]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 13004Cyclopropyl methyl ketoneHCID 76122Methyl cyclopropanecarboxylateHCID 10942334Sodium Methoxide

생성물 1

HCID 137807821,3-Dicyclopropylpropane-1,3-dione수율 78%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 1140Toluene용매

반응 조건

온도
55 °C

실험 절차

Methylcyclopropanecarboxylate (20.2 ml, 286.3 mmol) was added to a stirred solution of 1-cyclopropylethanone (9 ml, 152.4 mmol) in dimethylsulfoxide (25 ml). Sodium methoxide powder (10.8 g, 200 mmol) was added, and the reaction was stirred at 55° C. for 8 hours. The mixture was cooled, diluted with toluene, neutralised with 6M hydrochloric acid, and then extracted with toluene. The combined extracts were washed with sodium carbonate, dried over magnesium sulphate and evaporated in vacuo to provide the title compound (14.9 g, 78%) as a mixture 2:1 enol:ketone forms. 1H NMR (CDCl3, 400 MHz): δ=0.79-0.87 (m, 4H), 0.98-1.01 (m, 4H), 1.46-1.51 (m, 2H-enol), 1.93-1.97 (m, 2H-keto), 3.70 (s, 2H-keto), 5.65 (s, 1H-enol); LRMS: APCl+: m/z 153 [MH+]; APCl− m/z 151 [M−H]−.

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with toluene
  3. washThe combined extracts were washed with sodium carbonate
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-d77f97770b704a49882c66946ae20c7e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425569B2

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