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

HRID 2404028

反応式

HRID 2404028 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-632ed6630c1b4645904f4cde9d270cb6
出典データセット
uspto-grants-2014_08
特許番号
US08802697B2

関連ノート

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