Ethanol → Decane-4,7-dione

HRID 2103764

반응식

HRID 2103764 반응식
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]

참가 물질

6

반응물 5

HCID 702EthanolHCID 962WaterHCID 3283Diethyl Ether3회HCID 4379853N,N'-dimethoxy-N,N'-dimethylbutanediamideHCID 178455855HCID 178455855, 화합물

생성물 1

HCID 12210000Decane-4,7-dione

실험 절차

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) : 2.69 (s, 4H), 2.46 (t, J=7.4 Hz, 4H), 1.60˜1.67 (m, 4H), 0.935 (t, J=7.5 Hz, 6H).

후처리

  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

출처 및 근거

ORD 기록
ord-fba4260dbcb2495b921c6b232b5098c3
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576122B2

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