Diethyl Oxalate → Ethyl (3,5-dimethoxyphenyl)(oxo)acetate

HRID 2404028

반응식

HRID 2404028 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.C([Li])CCC.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

참가 물질

5

반응물 3

HCID 7268Diethyl OxalateHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 24722256Ethyl (3,5-dimethoxyphenyl)(oxo)acetate수율 71.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of 1-bromo-3,5-dimethoxybenzene (2.17 g, 10 mmol) in THF (15 mL) was dropwise added n-butyl lithium (8 mL, 2.5 mol/L in hexane, 20 mmol) at −78′C. After stirring for 50 mins at −78° C., a solution of diethyl oxalate (4 g, 27 mmol) in THF (10 mL) was added. The mixture was stirred at −78° C. for another 4 h, then quenched with saturated ammonium chloride and extracted with ethyl acetate (50 mL*3). The organic layers were combined, washed by brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel to give the title compound (1.7 g, 71%). MS (ES+) C12H14O5 requires: 238. found: 239 [M+H]+.

후처리

  1. stirringThe mixture was stirred at −78° C. for another 4 h
  2. customquenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate (50 mL*3)
  4. washwashed by brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-632ed6630c1b4645904f4cde9d270cb6
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802697B2

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