Ethanol → Decane-4,7-dione

HRID 490800

反応式

HRID 490800 の反応式
CON(C)[C:4](=[O:13])[CH2:5][CH2:6][C:7](N(OC)C)=[O:8].[CH2:15]([Mg]Cl)[CH2:16][CH3:17].[CH2:20](O)[CH3:21].O.[CH3:24]COCC>>[CH3:15][CH2:16][CH2:17][C:4](=[O:13])[CH2:5][CH2:6][C:7](=[O:8])[CH2:24][CH2:20][CH3:21]

参加物

6

反応物 5

HCID 702EthanolHCID 962WaterHCID 3283Diethyl Ether3 回HCID 4379853N,N'-dimethoxy-N,N'-dimethylbutanediamideHCID 178455855HCID 178455855、化合物

生成物 1

HCID 12210000Decane-4,7-dione

実験手順

Cool a suspension of 20.42 g N,N′-dimethoxy-N,N′-dimethylsuccinamide from the Step A above in 1 L anhydrous ether in an ice bath under nitrogen. Add 300 mL of 2 M propylmagnesium chloride in ether over 15 minutes with mechanical stir. Continue to stir the reaction mixture in the cooling bath for 2.25 hours. Quench the reaction by adding 30 mL ethanol in 50 mL ether over 30 minutes. Pour the resulting suspension into 1 L ice and water containing 75 mL concentrated HCl. Separate the layers, wash the organic layer with dilute HCl, 5% NaHCO3 and saturated brine. Dry over anhydrous Na2SO4. Evaporate the clear yellowish solution to give the title compound as yellow solid. 1H NMR (CDCl3, 500 MHz) δ: 2.69 (s, 4H), 2.46 (t, J=7.4 Hz, 411), 1.60-1.67 (m, 4H), 0.935 (t, J=7.5 Hz, 61).

後処理

  1. temperatureCool
  2. customQuench
  3. customthe reaction
  4. customSeparate the layers
  5. washwash the organic layer with dilute HCl, 5% NaHCO3 and saturated brine
  6. dry with materialDry over anhydrous Na2SO4
  7. customEvaporate the clear yellowish solution

出典と根拠

ORDレコード
ord-dd2c7364bfe64c0593fbb870e3b9ba46
出典データセット
uspto-grants-2009_05
特許番号
US07528163B2

関連ノート

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