Water → Methyl 2-(4-t-butylphenyl)propanoate

HRID 1061136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061136
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[CH3:26]I.O>C1COCC1>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 605629Methyl p-tert-butylphenylacetateHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 10704172Methyl 2-(4-t-butylphenyl)propanoateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

23.3 mL of lithium bis(trimethylsilyl)amide (1.0 M, 23 mmols) was added dropwise to 4.75 g (23 mmols) of methyl 4-tert-butylphenylacetate in 100 mL of dry THF at −78° C. while stirring under nitrogen. The mixture was stirred at this temperature for 45 minutes, then 1.5 mL (24 mmol) methyl iodide was added dropwise and the solution was stirred for an additional 1 hour at −78° C. The mixture was poured into 200 mL of H2O and the desired product was extracted with 500 mL diethyl ether. The organic layer was backwashed once with 500 mL H2O, dried over K2CO3, and concentrated under reduced pressure to yield 5.12 of a dark oil. The oil was purified via silica gel chromatography eluting with a solvent gradient of hexane to hexane/ethyl acetate 19:1. The fractions containing the desired product were combined and concentrated under reduced pressure to yield the title compound 2.65 g (53%).

Aufarbeitung

  1. stirringThe mixture was stirred at this temperature for 45 minutes
  2. stirringthe solution was stirred for an additional 1 hour at −78° C
  3. extractionthe desired product was extracted with 500 mL diethyl ether
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated under reduced pressure
  6. customto yield 5.12 of a dark oil
  7. customThe oil was purified via silica gel chromatography
  8. washeluting with a solvent gradient of hexane to hexane/ethyl acetate 19:1
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8080724dd23d41d1b10d05d68c8f7030
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525099B1

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