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

HRID 31153

反応式

HRID 31153 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 137807821,3-Dicyclopropylpropane-1,3-dione収率 78%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 1140Toluene溶媒

反応条件

温度
55 °C

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-d77f97770b704a49882c66946ae20c7e
出典データセット
uspto-grants-2008_09
特許番号
US07425569B2

関連ノート

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