Diethyl Oxalate → 2,4-Dioxo-5-phenoxy-hexanoic acid ethyl ester

HRID 2046180ノート

反応式

HRID 2046180 の反応式
[Na].[O:2]([CH:9]([CH3:13])[C:10](=[O:12])[CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CCO>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[O:20])[CH2:11][C:10](=[O:12])[CH:9]([O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:13])[CH3:19]

参加物

5

反応物 3

HCID 7268Diethyl OxalateHCID 27644743-Phenoxy-2-butanoneHCID 5360545Sodium2 回

生成物 1

HCID 679746002,4-Dioxo-5-phenoxy-hexanoic acid ethyl ester収率 66.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

Sodium (82 mg, 3.55 mmol) was added to EtOH absolute (9.8 mL) at 0° C. The mixture was stirred at 0° C. until the sodium was completely dissolved. Then (rac)-3-phenoxy-butan-2-one (530 mg, 3.23 mmol) was added dropwise. The mixture was stirred at 0° C. for 10 minutes. Then diethyl oxalate (0.44 mL, 3.23 mmol) was added. Then the mixture was stirred at room temperature for 16 hours and the solvent evaporated in vacuo. The residue was diluted with water, the mixture acidified with a 1M solution of HCl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by open column chromatography (silica; DCM 100%) to yield (rac)-2,4-dioxo-5-phenoxy-hexanoic acid ethyl ester (566 mg, 58% yield) as an orange oil.

後処理

  1. dissolutionwas completely dissolved
  2. stirringThen the mixture was stirred at room temperature for 16 hours
  3. customthe solvent evaporated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with DCM
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvents evaporated in vacuo
  10. customThe crude product was purified by open column chromatography (silica; DCM 100%)

出典と根拠

ORDレコード
ord-69f8725c59d1439fa42b0bbbcabbe8db
出典データセット
uspto-grants-2013_11
特許番号
US08592422B2

反応ノート

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