Chlorodifluoromethane → (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

HRID 1449846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449846
C([O:5][C:6]([CH:8]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:9](OCC)=O)=O)(C)(C)C.CC(C)([O-])C.[Na+].ClC(F)[F:31].O.[Cl-].[Na+].O>O1CCCC1>[F:31]/[CH:9]=[C:8](\[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)/[CH2:6][OH:5]

Komponenten

6

Edukt 4

HCID 6372ChlorodifluoromethaneHCID 15342050Ethyl 2-(t-butoxycarbonyl)-4-(p-fluorophenyl)butyrateHCID 23676156Sodium t-butoxideHCID 23713072Sodium chloride dihydrate

Produkt 1

HCID 10943450(E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Combine ethyl 2-(t-butoxycarbonyl)-4-(p-fluorophenyl)butyrate (32.14 g) and sodium t-butoxide (19.81 g) in tetrahydrofuran (400 mL). Stir the mixture for 1 hour, then heat to 45° C. Add an excess of chlorodifluoromethane over about 15 minutes. After 1 hour under an atmosphere of chlorodifluoromethane, allow the temperature to fall to ambient. Pour the reaction mixture into water/brine. Extract with diethyl ether. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Aufarbeitung

  1. waitAfter 1 hour under an atmosphere of chlorodifluoromethane
  2. extractionExtract with diethyl ether
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8e581fb653ac44c3bb8cb95a9dfb5aa9
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599986

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