Ethanol → Ethyl 6-[(4,4,5,5,5-pentafluoropentyl)oxy]hexanoate

HRID 459684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459684
CC1C=CC(S([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])(=O)=O)=CC=1.[F:22][C:23]([F:32])([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:25][CH2:26]O.CC(C)([O-])C.[K+].C(O)C>O1CCCC1>[F:22][C:23]([F:32])([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:25][CH2:26][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 5479674,4,5,5,5-Pentafluoropentan-1-olHCID 11056130Hexanoic acid, 6-[[(4-methylphenyl)sulfonyl]oxy]-, ethyl esterHCID 23665647Potassium tert-butoxide2×

Produkt 1

HCID 18444112Ethyl 6-[(4,4,5,5,5-pentafluoropentyl)oxy]hexanoateAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

To a stirred solution of the product of step (a) (500 mg) and 4,4,5,5,5-pentafluoropentan-1-ol (284 mg) in tetrahydrofuran (10 ml) was added potassium tert-butoxide (1M in tetrahydrofuran; 1.6 ml) and the reaction was stirred at 200° C. for 2 hours. An additional charge of potassium tert-butoxide (1M in tetrahydrofuran; 1.6 ml) was added and the reaction was stirred for a further 18 hours. Ethanol (5 ml) was added and the reaction was stirred for 30 mlnutes. The reaction mixture was partitioned between dichloromethane (300 ml) and water (300 ml). The organic layer was dried over magnesium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel (5 g Bond Elut cartridge) eluting with 20% ethyl acetate in cyclohexane gave the title compound as a clear oil (100 mg).

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred for a further 18 hours
  3. stirringthe reaction was stirred for 30 mlnutes
  4. customThe reaction mixture was partitioned between dichloromethane (300 ml) and water (300 ml)
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. customthe solvent was removed in vacuo
  7. customPurification by column chromatography on silica gel (5 g Bond Elut cartridge)
  8. washeluting with 20% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-5fc9b9c0de2443bb91b34f635e0d3e32
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07195752B2

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