Sodium Hydroxide → HCID 23695520, Verbindung

HRID 2232626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232626
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]>C(O)C.O>[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 2

HCID 14798Sodium HydroxideHCID 54007397HCID 54007397, Verbindung

Produkt 1

HCID 23695520HCID 23695520, VerbindungAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

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 ml 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) δ1.54 (2H, 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-81cf0ac80f9c45cc9ac017fe1808fb0b
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04788304

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