Methyl iodide → (R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

HRID 1643264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643264
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([OH:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:17].[CH3:18]I>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([O:16][CH3:18])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:17]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 42077386(R)-4-(4-Fluoro-3-methyl-phenyl)-4-hydroxy-butanoic acid

Produkt 1

HCID 59568829(R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To the suspension of NaH (373 mg of a 60% dispersion in mineral oil, 9.3 mmol) in 20 mL THF was slowly added (R)-4-(4-Fluoro-3-methyl-phenyl)-4-hydroxy-butanoic acid as a solution in 10 mL THF at 25° C. Methyl iodide (974 mg, 6.9 mmol, 427 μL) was then added dropwise to the mixture. The resulting mixture was stirred for 3 h at room temperature and then the reaction was quenched by the addition of 20 mL of 1M HCl. The mixture was and extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent left the crude product as an oil which was used in the next step without further purification.

Aufarbeitung

  1. customat 25° C
  2. customthe reaction was quenched by the addition of 20 mL of 1M HCl
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washthe combined organic layers washed with brine (2×20 mL)
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of solvent
  7. waitleft the crude product as an oil which
  8. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-aecb9b0a7df74de593857e3ba316a2c8
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119692B2

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