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Methyl iodide → 4-(Tert-butoxy)-3-methyl-4-oxobutanoic acid

HRID 1469655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1469655
[Li+].[CH3:2]C([N-]C(C)C)C.[C:9]([O:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])([CH3:12])([CH3:11])[CH3:10].CI>C1COCC1>[C:9]([O:13][C:14](=[O:20])[CH:15]([CH3:2])[CH2:16][C:17]([OH:19])=[O:18])([CH3:12])([CH3:10])[CH3:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 41391074-(Tert-butoxy)-4-oxobutanoic acid

Produkt 1

HCID 127614644-(Tert-butoxy)-3-methyl-4-oxobutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a stirred solution of LDA (6.3 mmol, 2M in hexane) in THF (5 mL) at −78° C. is added a solution of succinic acid mono-tert-butyl ester (523 mg, 3 mmol) in THF (2 mL) dropwise. After the addition, the mixture is warmed to −20° C. slowly and stirred at −20° C. for 30 minutes. The solution is re-cooled to −78° C. and MeI (511 mg, 3.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred for 18 hours. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give 2-methyl-succinic acid 1-tert-butyl ester.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThe solution is re-cooled to −78° C.
  3. temperatureThe mixture is warmed to room temperature
  4. stirringstirred for 18 hours
  5. customThe mixture is quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with water, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-af28f5bea6b24a6d801882b8c216124b
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09006249B2

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