Hydrochloric Acid → Ethyl 4-(4-Methoxybenzyl)acetoacetate

HRID 256191

Reaktionsgleichung

Reaktionsgleichung von HRID 256191
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].C([Li])CCC.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.Cl>O1CCCC1.CCCCCC>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][CH2:7][C:5](=[O:6])[CH2:4][C:3]([O:9][CH2:10][CH3:11])=[O:8])=[CH:21][CH:20]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8868Ethyl Acetoacetate2×HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 178418339Butyllithium

Produkt 1

HCID 9992286Ethyl 4-(4-Methoxybenzyl)acetoacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Into a 3 l. 3-necked r.b. flask equipped with a mechanical stirrer, thermometer, dropping funnel, and nitrogen gas inlet was placed 24 g. (0.5 mole) of 50% NaH prewashed with hexane, and 1000 ml. of dry tetrahydrofuran. 65 g. (0.5 mole) of ethyl acetoacetate was then added dropwise at -10° to 0° C. using a dry ice-acetone bath. After addition of ethyl acetoacetate was finished, the mixture was gradually warmed up to 10° C. in the course of 15 minutes and then 240 ml. (0.528 mole) of 2.2M n-butyllithium was added dropwise maintaining temperature below -40° to -20° C. After the mixture was stirred at -10° for 15 minutes, 100.5 g. (0.5 mole) of 4-methoxybenzyl bromide was added dropwise over a period of 45 minutes at -10° C. The reaction mixture was gradually warmed up to room temperature and stirred for an additional hour, and then cooled to -20° C. 5N HCl was then carefully added until the solution was slightly acidic.

Aufarbeitung

  1. customflask equipped with a mechanical stirrer
  2. temperaturemaintaining temperature below -40° to -20° C
  3. temperatureThe reaction mixture was gradually warmed up to room temperature
  4. stirringstirred for an additional hour
  5. temperaturecooled to -20° C

Quellen und Nachweise

ORD-Eintrag
ord-4961895a58a5443da5f69caf82186bac
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04701461

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