Methyl iodide → (S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoic acid

HRID 1643282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643282
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([OH:19])[CH2:11][C@H:12]([CH2:16][CH:17]=[CH2:18])[C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:20].[CH3:21]I>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([O:19][CH3:21])[CH2:11][C@H:12]([CH2:16][CH:17]=[CH2:18])[C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:20]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59568774(S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-hydroxyethyl)pent-4-enoic acid

Produkt 1

HCID 59568837(S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a suspension of 217 mg NaH in 20 mL THF was added (S)-2-((R)-2-(4-fluoro-3-methylphenyl)-2-hydroxyethyl)pent-4-enoic acid in 5 mL THF slowly at room temperature. To this mixture was added methyl iodide (289 μL) dropwise followed by stirring for 3 h at 25° C. The reaction was quenched by the addition of 10 mL 1M HCl and then extracted with ethylacetate (3×30 mL). The combined organic layers were washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent afforded an oil which was used without further purification in the next reaction.

Aufarbeitung

  1. customThe reaction was quenched by the addition of 10 mL 1M HCl
  2. extractionextracted with ethylacetate (3×30 mL)
  3. washThe combined organic layers were washed with brine (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvent
  6. customafforded an oil which
  7. customwas used without further purification in the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-9d82caf123ad422a898567ab32e2940e
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119692B2

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