Hydrochloric Acid → 4-(3-Fluorophenyl)butanoic acid

HRID 971271ノート

反応式

HRID 971271 の反応式
C[O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)=O.O.NN.[OH-].[K+].Cl>C(O)CO.O.CCOCC>[F:14][C:10]1[CH:9]=[C:8]([CH2:6][CH2:5][CH2:4][C:3]([OH:15])=[O:2])[CH:13]=[CH:12][CH:11]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 12465650Methyl 4-(3-fluorophenyl)-4-oxobutanoate

生成物 1

HCID 149151134-(3-Fluorophenyl)butanoic acid収率 75.3%

試薬・触媒・溶媒 3

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 4-(3-fluoro-phenyl)-4-oxo-butyric acid methyl ester (28.27 g, 134.49 mmol), hydrazine monohydrate (26.1 mL, 26.93 g, 537.96 mmol) and KOH (22.64 g, 403.47 mmol) in ethylene glycol (150 mL) was heated to reflux under argon and refluxed for 2 hours. The reaction mixture was cooled and diluted with 1.5 litres of water, 500 mL of Et2O was added, and the mixtures was acidified by addition of 6 M HCl with stirring, after which an additional 500 mL of Et2O was added. The organic layer was removed and the aqueous layer was extracted twice with 250 mL of 500 mL of Et2O/EtOAc (3:1). The combined organic layers were washed with water, saturated brine, and then dried over MgSO4. The solvent was evaporated under reduced pressure to yield a brownish oil, which was eluted through silica gel using hexanes/EtOAc (9:1). Removal of solvent under reduced pressure yielded 18.44 g (101.21 mmol, 75.26%) of 4-(3-fluoro-phenyl)-butyric acid as an oil. MS: 183 (M+H)+.

後処理

  1. temperatureto reflux under argon
  2. temperaturerefluxed for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. additionwas added
  5. customThe organic layer was removed
  6. extractionthe aqueous layer was extracted twice with 250 mL of 500 mL of Et2O/EtOAc (3:1)
  7. washThe combined organic layers were washed with water, saturated brine
  8. dry with materialdried over MgSO4
  9. customThe solvent was evaporated under reduced pressure
  10. customto yield a brownish oil, which
  11. washwas eluted through silica gel
  12. customRemoval of solvent under reduced pressure

出典と根拠

ORDレコード
ord-708f2a61361e42cabea60dacbdea970f
出典データセット
uspto-grants-2007_12
特許番号
US07312359B2

反応ノート

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