Water → Methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate

HRID 129707

Reaktionsgleichung

Reaktionsgleichung von HRID 129707
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20](OC)=[O:21].[H-].[Na+].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[CH:20][OH:21])[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetate

Produkt 1

HCID 69942437Methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of methyl 2-benzyloxyphenylacetate (26.99 g) and methyl formate (126.62 g) in dry DMF (300 ml) was added dropwise to a stirred suspension of sodium hydride (50% disp. in oil, 10.13 g) in DMF (300 ml) at 0° C. After stirring at 0° C. for two hours the mixture was poured into water (1000 ml) and washed with ether (2×150 ml). The aqueous layer was acidified to pH4 with 6M hydrochloric acid then extracted with ether (2×350 ml). The extracts were dried and concentrated under reduced pressure to afford crude methyl 2-[2'-benzyloxyphenyl]-3-hydroxyacrylate as a yellow oil, infrared max. (film): 1720, 1660 cm-1.

Aufarbeitung

  1. washwashed with ether (2×150 ml)
  2. extractionthen extracted with ether (2×350 ml)
  3. customThe extracts were dried
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-08ab360af7ae4880a33cc9a07e18d6d7
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470819

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