Acetone → 1-Cyclobutylbutane-1,3-dione

HRID 42476

반응식

HRID 42476 반응식
[CH:1]1([C:5]([O:7]CC)=O)[CH2:4][CH2:3][CH2:2]1.[CH3:10][C:11]([CH3:13])=[O:12]>CCOCC>[CH:1]1([C:5](=[O:7])[CH2:10][C:11](=[O:12])[CH3:13])[CH2:2][CH2:3][CH2:4]1

참가 물질

4

반응물 2

HCID 180AcetoneHCID 84700Ethyl cyclobutanecarboxylate

생성물 1

HCID 552735631-Cyclobutylbutane-1,3-dione수율 76%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of NaNH2 (11.7 g, 91 mmol) in anhydrous ether (150 mL) under N2 at 30° C. was added dropwise a mixture of ethyl cyclobutanecarboxylate (19.2 g, 150 mmol) and acetone (21.75 g, 375 mmol). After addition, the reaction mixture was stirred for 4 h, then poured onto ice water with stirring. Ether was added and the unreacted components were extracted into the organic phase. The clear aqueous extract was acidified to pH 5.0 with 2 N HCl, and then to pH 7.5 with Na2CO3. The solution was extracted with ether. The combined organic layers were dried (Na2SO4), filtered, and concentrated to give the crude product of 1-cyclobutyl-1,3-butanedione (9.7 g, 76%), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3-d3) δ 5.42 (s, 1H), 3.66 (s, 1H), 2.11-2.23 (m, 4H), 2.02 (s, 3H), 1.93-1.99 (m, 2H).

후처리

  1. additionAfter addition
  2. additionpoured onto ice water
  3. stirringwith stirring
  4. extractionthe unreacted components were extracted into the organic phase
  5. extractionThe clear aqueous extract
  6. extractionThe solution was extracted with ether
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-def4a5b9e99e411a9af117e89af99194
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536179B2

연결된 노트

불러오는 중…