Water → Ethyl 2-hydroxycyclopentanecarboxylate

HRID 2214059

Reaktionsgleichung

Reaktionsgleichung von HRID 2214059
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])=[O:5])[CH3:2].[BH4-].[Na+].O>C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[OH:11])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 4311764Sodium borohydride

Produkt 1

HCID 275611Ethyl 2-hydroxycyclopentanecarboxylateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-oxo-cyclopentanecarboxylic acid ethyl ester (10 g, 64.0 mmol) in ethanol (106.7 mL) cooled to 0° C. was treated with 98% sodium borohydride (686 mg, 17.78 mmol). The reaction was stirred at 0° C. for 30 min. At this time, the reaction mixture was poured into water (53 mL) and was extracted into diethyl ether (3×100 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 75/25 ethyl acetate/hexanes) afforded 2-hydroxy-cyclopentanecarboxylic acid ethyl ester (8.5 g, 83.9%) as a clear liquid.

Aufarbeitung

  1. extractionwas extracted into diethyl ether (3×100 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f468ddf4ab0b415abdb51b41a538aafa
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105671B2

Verknüpfte Notizen

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