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

HRID 1013568노트

반응식

HRID 1013568 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 149151134-(3-Fluorophenyl)butanoic acid수율 75.3%

시약·촉매·용매 3

HCID 174Ethylene Glycol용매HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3b1aa1f8d8754898a2ffe891d97b9576
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981923B2

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