Hydrochloric Acid → 2-[4-(2-Methylbutyryl)benzyl]anisole

HRID 895649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895649
C(N(CC)[C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:8][CH:7]=1)=[O:5])C.[CH:23]([Li])([CH2:25][CH3:26])[CH3:24].Cl>C1(C)C=CC=CC=1.CCCCCC.C1CCCCC1>[CH3:24][CH:23]([CH2:25][CH3:26])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:19][CH:20]=1)=[O:5]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 223806822-(4-Diethylcarbamoylbenzyl)anisoleHCID 178418400CID 53628100

Produkt 1

HCID 223805962-[4-(2-Methylbutyryl)benzyl]anisoleAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

The 2-(4-diethylcarbamoylbenzyl)anisole (100 mg) obtained in the process of Reference Example 1(d) was dissolved in toluene (2 ml), added with a solution of sec-butyl lithium in n-hexane and cyclohexane (1.0 M, 0.47 ml) at 0° C. under argon atmosphere and stirred at room temperature for 1 hour. After the reaction mixture was slowly poured into 1 N aqueous hydrochloric acid (5 ml) with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with ether (10 ml). The organic layer was washed with saline and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1) to obtain 58.3 mg of the title compound. Yield: 61%.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with ether (10 ml)
  5. washThe organic layer was washed with saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-74a497591a954d9d989c51a3d92f9b12
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916822B2

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