Cyclooctanone → Ethyl 2-oxocyclononanecarboxylate

HRID 21961

반응식

HRID 21961 반응식
[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.C([O+](CC)CC)C.[N+](=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N-]>C(Cl)Cl>[CH2:28]([O:27][C:25]([CH:24]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:1]1=[O:9])=[O:26])[CH3:29]

참가 물질

5

반응물 3

HCID 10403CyclooctanoneHCID 12192Ethyl diazoacetateHCID 2723982Triethyloxonium tetrafluoroborate

생성물 1

HCID 107210Ethyl 2-oxocyclononanecarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Cyclooctanone (25 g, 198 mmol) is dissolved in methylene chloride (500 mL) and the solution is cooled to 0° C. Triethyloxonium tetrafluoroborate (121.6 g, 640 mmol) is added. Ethyl diazoacetate (41.61 g, 365 mmol) is then added dropwise over 25 minutes, and the reaction is stirred at 0° C. for 4 hours. The reaction is quenched by pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L) and stirring overnight. The reaction mixture is then extracted several times with methylene chloride, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by vacuum distillation (0.2-1.0 mm Hg) and the fraction boiling between 100°-125° C. is collected to give 2-ethoxycarbonyl-cyclononanone.

후처리

  1. customThe reaction is quenched
  2. additionby pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L)
  3. stirringstirring overnight
  4. extractionThe reaction mixture is then extracted several times with methylene chloride
  5. dry with materialthe combined organic layers are dried (Na2SO4)
  6. customthe solvent is evaporated
  7. distillationThe product is purified by vacuum distillation (0.2-1.0 mm Hg)
  8. customboiling between 100°-125° C.
  9. customis collected

출처 및 근거

ORD 기록
ord-e0c09bb1cb814c83a4a839f3b0263609
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426103

연결된 노트

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