Boronic Acid → Ethyl 5,5,5-trifluoro-4-oxopentanoate

HRID 216685노트

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HRID 216685 반응식
C(OC(=O)[CH:5]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])C.B(O)O>C(O)C>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH3:11]

참가 물질

4

반응물 2

HCID 61668Boronic AcidHCID 11346247Butanedioic acid, (trifluoroacetyl)-, diethyl ester

생성물 1

HCID 13379932Ethyl 5,5,5-trifluoro-4-oxopentanoate수율 43.2%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
170 °C

실험 절차

In a one-necked round-bottomed flask equipped with a distillation head and cooler, a mixture of 2-(2,2,2-trifluoro-acetyl)-succinic acid diethyl ester (54.6 g, 202 mmol) and boronic acid (12.5 g, 202 mmol) is heated to 170° C. Heating is continued for4 h, during which time ethanol is gradually distilled off as it is formed. After cooling to room temperature, the reaction mixture is poured onto ice and extracted twice with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4 and concentrated at reduced pressure to afford a brown oil. The crude product is purified by distillation (60° C., 10 mbar) to afford the title compound as a colorless liquid (17.3 g, 87.3 mmol, 43%). 1H NMR (400 MHz, CDCl3, 298 K): δ=4.15 (q, J=7.1 Hz, 2H), 3.02 (t, J=6.4 Hz, 2H), 2.70 (t, J=6.4 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H). MS (ES+): 199 (M(C7H9F3O3)+H)+.

후처리

  1. customIn a one-necked round-bottomed flask equipped with a distillation head and cooler
  2. temperatureHeating
  3. distillationis gradually distilled off as it
  4. customis formed
  5. temperatureAfter cooling to room temperature
  6. additionthe reaction mixture is poured onto ice
  7. extractionextracted twice with EtOAc
  8. washThe combined organic layers are washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated at reduced pressure
  11. customto afford a brown oil
  12. distillationThe crude product is purified by distillation (60° C., 10 mbar)

출처 및 근거

ORD 기록
ord-90be355142b34bdc87e73564076c5443
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193236B2

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