Methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate → Methyl 2-(3-oxocyclobutyl)acetate

HRID 1966079

반응식

HRID 1966079 반응식
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[CH2:8][C:7](=[O:9])[C:6]1(Cl)Cl>CC(O)=O.[Zn]>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[CH2:8][C:7](=[O:9])[CH2:6]1

참가 물질

4

반응물 1

HCID 57686758Methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate

생성물 1

HCID 57686718Methyl 2-(3-oxocyclobutyl)acetate수율 36.2%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a solution of (2,2-dichloro-3-oxo-cyclobutyl)-acetic acid methyl ester (2.93 g, 13.8 mmol) in AcOH (100 ml), zinc powder (4.51 g, 69.0 mmol) is added. The mixture is stirred at 100° C. for 15 hours. The mixture is filtrated and washed with AcOH. The filtrate is concentrated under reduced pressure, and the residue is dissolved in AcOEt, and washed with saturated aqueous NaHCO3 and brine. The organic layer is dried over MgSO4, and concentrated under reduced pressure to give (3-oxo-cyclobutyl)-acetic acid methyl ester (710 mg, 36%); 1H NMR (400 MHz, chloroform-d) δ ppm 2.64-2.66 (m, 2H), 2.78-2.86 (m, 3H), 3.22-3.32 (m, 2H), 3.70 (s, 3H).

후처리

  1. filtrationThe mixture is filtrated
  2. washwashed with AcOH
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in AcOEt
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e0cda268fac64acead7c07115c4799d9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420641B2

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