Water → 2-(1-cyclopropylethoxy)Acetic acid

HRID 376353

Reaktionsgleichung

Reaktionsgleichung von HRID 376353
[H-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].[CH3:8][CH:9]([CH:11]1[CH2:13][CH2:12]1)[OH:10].O>C1COCC1>[CH:11]1([CH:9]([O:10][CH2:4][C:5]([OH:7])=[O:6])[CH3:8])[CH2:13][CH2:12]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 791041-Cyclopropylethanol

Produkt 1

HCID 221142352-(1-cyclopropylethoxy)Acetic acidAusbeute 29,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of NaH (80% in oil) (15.7 g, 523 inmol) in THF (180 mL) at 0° C. were added bromoacetic acid (28.0 g, 203 mmol) and a-methylcyclopropane methanol (10.0 g, 116 mmol). The resulting mixture was then stirred at 70° C. After a period of 18 h, the reaction mixture was poured over cold H2O and the H2O phase was extracted once with Et2O. The water phase was acidified with HCl and extracted twice with Et2O. The ether was dried over MgSO4, filtered and evaporated under reduced pressure. The crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH) to provide 5.0 g of the title compound.

Aufarbeitung

  1. extractionthe H2O phase was extracted once with Et2O
  2. extractionextracted twice with Et2O
  3. dry with materialThe ether was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH)

Quellen und Nachweise

ORD-Eintrag
ord-ea01a07f1b7b437c8165fa26e3c444d7
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020343

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