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

HRID 2046180

반응식

HRID 2046180 반응식
[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]

참가 물질

5

반응물 3

HCID 7268Diethyl OxalateHCID 27644743-Phenoxy-2-butanoneHCID 5360545Sodium2회

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-69f8725c59d1439fa42b0bbbcabbe8db
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592422B2

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