Formaldehyde → Ethyl 2,2-difluoro-3-hydroxypropanoate

HRID 1032914

Reaktionsgleichung

Reaktionsgleichung von HRID 1032914
[CH2:1]=[O:2].[F:3][C:4]([F:11])(Br)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl-].[NH4+]>O1CCCC1.[Zn]>[F:3][C:4]([F:11])([CH2:1][OH:2])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 69585Ethyl bromodifluoroacetate

Produkt 1

HCID 2758828Ethyl 2,2-difluoro-3-hydroxypropanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of paraformaldehyde (4.5 g, 50 mmol), ethyl difluorobromoacetate (10.2 g, 50 mmol) and activated zinc dust (3.3 g, 40 mmol) in anhydrous tetrahydrofuran was heated under reflux for 0.5 h. Then the mixture was treated with a saturated aqueous solution of ammonium chloride and extracted with diethyl ether. After usual work-up the desired compound ethyl 2,2-difluoro-3-hydroxypropionate was obtained by flash chromatography on silica gel (ethyl acetate:hexane; 25:75) (4.1 g, 53%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 h
  3. extractionextracted with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ac3fae5763854e80b28e6ae53fb8b8f9
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05308837

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