Water → HCID 23695520, Verbindung

HRID 2232657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232657
C[O:2][C:3]([C:5]1([CH:8]([F:21])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:7][O:6]1)=[O:4].[OH-].[Na+:23].O>C(O)C>[Na+:23].[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([C:5]2([C:3]([O-:4])=[O:2])[CH2:7][O:6]2)[F:21])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54007397HCID 54007397, Verbindung

Produkt 1

HCID 23695520HCID 23695520, VerbindungAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-[5-(4-chlorophenoxy)-1-fluoropentyl]-2-oxiranecarboxylic acid methyl ester (2.53 g, 8 mmol) of Example 2 in 25 ml of absolute ethanol is treated with a solution of 320 mg (8 mmol) of sodium hydroxide in 12 m l of water. The mixture is maintained with stirring at room temperature for 2 hours and then is rotoevaporated. The obtained solid is triturated three times with ethyl ether, the solvent is removed by rotoevaporation and the solid is dried at high vacuum over phosphorus pentoxide to give 2.25 g (86.6%) of the title compound: m.p. 159°-175° C.; IR (KBr) 1630, 1608, 1490 and 1242 cm-1 ; NMR (d6 -DMSO) δ 1.54 (2H, m), 1.73 (4H, m), 1.73 (4H, m), 2.65 (1H, m), 2.73 (1H, d, J=6 Hz), 3.98 (2H, t, J=6 Hz), 5.22 (1H, ddd, JHF =48, 10, 3 Hz), 7.00 (2H, d, J=9 Hz) and 7.36 (2H, d, J=9 Hz).

Aufarbeitung

  1. temperatureThe mixture is maintained
  2. customThe obtained solid is triturated three times with ethyl ether
  3. customthe solvent is removed by rotoevaporation
  4. dry with materialthe solid is dried at high vacuum over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-f89e00dea67a415c9c289cc10e90e37b
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04788306

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