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Trifluoroacetic acid → HCID 66839473、化合物

HRID 546791
ノート
印刷プレビュー

反応式

HRID 546791 の反応式
[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21])[CH2:5][CH2:6][C:7]([O:9]C(C)(C)C)=O.F[C:26](F)(F)C(O)=O>ClCCl>[O:9]=[C:7]([CH3:26])[CH2:6][CH2:5][CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:21])([F:22])[F:23])[C:3]([O:2][CH3:1])=[O:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 66839325HCID 66839325、化合物

生成物 1

HCID 66839473HCID 66839473、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(2-Trifluoromethylphenyl)pentanedioic acid 5-tert-butyl ester 1-methyl ester (3 g) was dissolved in dichloromethane (30 mL). Trifluoroacetic acid (12 mL) was added and the reaction solution was stirred at room temperature for one hour. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in toluene (60 mL). Thionyl chloride (1.89 mL) was added and the reaction solution was stirred at 80° C. for three hours. The reaction solution was concentrated under reduced pressure and diluted with THF (50 mL). Then, tributylphosphine (2.37 mL) was added at −20° C. and the reaction solution was stirred for 20 minutes. A 0.97 M solution of methylmagnesium bromide in THF (9.78 mL) was added dropwise to the reaction solution, and the reaction solution was stirred for 15 minutes. Then, a 1 N hydrochloric acid aqueous solution was added, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (carrier: Chromatorex Si; elution solvent: heptane:ethyl acetate=19:1→heptane:ethyl acetate=1:1) to obtain the title compound (728 mg). The property values of the compound are as follows.

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in toluene (60 mL)
  3. additionThionyl chloride (1.89 mL) was added
  4. stirringthe reaction solution was stirred at 80° C. for three hours
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. additiondiluted with THF (50 mL)
  7. additionThen, tributylphosphine (2.37 mL) was added at −20° C.
  8. stirringthe reaction solution was stirred for 20 minutes
  9. additionA 0.97 M solution of methylmagnesium bromide in THF (9.78 mL) was added dropwise to the reaction solution
  10. stirringthe reaction solution was stirred for 15 minutes
  11. additionThen, a 1 N hydrochloric acid aqueous solution was added
  12. extractionfollowed by extraction with ethyl acetate
  13. dry with materialThe organic layer was dried over magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by silica gel chromatography (carrier: Chromatorex Si; elution solvent: heptane:ethyl acetate=19:1→heptane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-5709dbb4b112437e972190c148155caa
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07935815B2

反応ノート

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