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Hydrochloric Acid → [Rac]-3-(4-benzyloxy-benzofuran-7-yl)-2-ethoxy-propionic acid methyl ester

HRID 479196
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 479196
[Mg].[CH2:2]([O:4][C:5](=[O:28])/[C:6](/[O:25][CH2:26][CH3:27])=[CH:7]/[C:8]1[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:9]=1)C.[H][H].Cl>CO.C1COCC1>[CH3:2][O:4][C:5](=[O:28])[CH:6]([O:25][CH2:26][CH3:27])[CH2:7][C:8]1[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[C:11]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:10][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5462224Magnesium2×HCID 686170643-(4-Benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 68617324[Rac]-3-(4-benzyloxy-benzofuran-7-yl)-2-ethoxy-propionic acid methyl esterAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Magnesium turnings (0.5 g, 20.6 mmol) were added to a stirred solution of 3-(4-benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester (0.8 g, 2.18 mmol) in methanol (26 ml) and THF (13 ml) at ambient temperature. The suspension was warmed to 40° C. until evolution of hydrogen commenced. Then, the heating bath was replaced by a water bath, additional magnesium turnings (1 g, 41.2 mmol) were added and stirring of the reaction mixture was continued for 12 h. The suspension was cooled to 0° C., then 25% aqueous hydrochloric acid was added till all the solid had dissolved. The mixture was extracted twice with ethyl acetate and the combined ethyl acetate solutions were washed three times with water and dried over sodium sulfate. The solvent was evaporated to afford the title compound (0.77 g, 2.16 mmol, 99%) which was used in the next stage without further purification.

Aufarbeitung

  1. customThen, the heating bath was replaced by a water bath
  2. dissolutionhad dissolved
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. washthe combined ethyl acetate solutions were washed three times with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-df8cf065d30c4d2889d665dfe071e82b
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06642389B2

Notizen zur Reaktion

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