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

HRID 402904ノート

反応式

HRID 402904 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 13379932Ethyl 5,5,5-trifluoro-4-oxopentanoate収率 43.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
170 °C

実験手順

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 for 4 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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-715a9f1dc86d4bf6b8c027be82a75155
出典データセット
uspto-grants-2014_06
特許番号
US08742132B2

反応ノート

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