tert-Butanol → 2-(4-Fluorobenzyl)acetoacetic acid ethyl ester

HRID 2266459노트

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HRID 2266459 반응식
CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH2:12]([O:14][C:15](=[O:20])[CH2:16][C:17](=[O:19])[CH3:18])[CH3:13].Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1>O1CCCC1.O>[CH2:12]([O:14][C:15](=[O:20])[CH:16]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:17](=[O:19])[CH3:18])[CH3:13]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 8868Ethyl AcetoacetateHCID 96024-Fluorobenzyl chlorideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 27695652-(4-Fluorobenzyl)acetoacetic acid ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
15 °C

실험 절차

A suspension of potassium tert-butoxide (11.2 g) in anhydrous tetrahydrofuran (200 mL) at 0° C. was treated with a mixture of tert-butanol (0.2 mL) and 3-oxobutyric acid ethyl ester (12.7 mL). The mixture was warmed to 15° C. over a period of 40 minutes and a solution of 1-chloromethyl-4-fluorobenzene (11.9 mL) in tetrahydrofuran (40 mL) was added and the resulting mixture heated at 70° C. for 20 hours. The mixture was cooled to room temperature, diluted with water and the tetrahydrofuran removed under reduced pressure. The residue was extracted with ethyl acetate and the combined extracts washed with water and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by distillation under reduced pressure (boiling point, 102-104° C. at 0.42 mbar) to afford title compound as a colourless oil, 12.4 g.

후처리

  1. temperaturethe resulting mixture heated at 70° C. for 20 hours
  2. temperatureThe mixture was cooled to room temperature
  3. customthe tetrahydrofuran removed under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe combined extracts washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. distillationthe residue purified by distillation under reduced pressure (boiling point, 102-104° C. at 0.42 mbar)

출처 및 근거

ORD 기록
ord-2b0209d4b4e3454a92b64dc931f41477
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858640B2

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