Methyl iodide → HCID 12425357, Verbindung

HRID 610467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610467
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:17]([Li])CCC.IC>C1COCC1>[O:4]=[C:3]([CH2:5][CH3:17])[CH2:2][C:1]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 142266Benzyl acetoacetateHCID 178418339Butyllithium

Produkt 1

HCID 12425357HCID 12425357, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Following the procedure of Weiler, J. Am. Chem. Soc. 1974, 96, 1082, benzyl acetoacetate, 7.68 g (40 mmol) was added dropwise to a 0° C. suspension of sodium hydride (2.1 g of 50% dispersion, 42 mmol) in THF (100 mL). After stirring for 10 minutes n-butyl lithium (16 mL of 2.5 M in hexane) was added and the mixture was aged for an additional 10 minutes. At this time iodomethane (2.74 mL, 44 mmol) in THF (4 mL) was added dropwise and the mixture aged 1 hour while slowly warming to room temperature. Work-up was achieved by quenching at 0° C. with 1N HCl, extracting with ether, washing the ether with aqueous NaHCO3, brine, and drying with MgSO4. Removal of the solvent yielded benzyl 3-oxopentanoate.

Aufarbeitung

  1. additionwas added
  2. waitthe mixture aged 1 hour
  3. customby quenching at 0° C. with 1N HCl
  4. extractionextracting with ether
  5. washwashing the ether with aqueous NaHCO3, brine
  6. dry with materialdrying with MgSO4
  7. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-db6f33b4d57d44f385a24e130604ee9b
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998612

Notizen zur Reaktion

Wird geladen…