Methyl iodide → HCID 20272630, Verbindung

HRID 371368

Reaktionsgleichung

Reaktionsgleichung von HRID 371368
[CH2:1]([Mg]Cl)C(C)C.C(Cl)C(C)C.[Mg].[F:13][C:14]([F:26])([F:25])[CH:15]([OH:24])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CI>CCOCC.[CH-]1[C-]=[C-][C-]=[C-]1.[CH-]1[C-]=[C-][C-]=[C-]1.Cl[Ti]Cl>[F:13][C:14]([F:25])([F:26])[CH:15]([OH:24])/[CH:16]=[C:17](\[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)/[CH3:1]

Komponenten

8

Edukt 5

HCID 6328Methyl iodideHCID 10554Isobutyl chlorideHCID 5462224MagnesiumHCID 114129783-Butyn-2-ol, 1,1,1-trifluoro-4-phenyl-HCID 178418368HCID 178418368, Verbindung

Produkt 1

HCID 20272630HCID 20272630, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 416358Bis(cyclopentadienyl)titanium(IV) chlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In an isobutylmagnesium chloride solution that was prepared by reacting isobutyl chloride (3.74 g, 40 mmol) and magnesium (0.97 g, 40 mmol) in dry ether (40 ml) at 0° C., dichlorobis(π-cyclopentadienyl)titanium (0.22 g, 0.9 mmol) and 1,1,1-trifluoro-4-phenyl-3-butyne-2-ol (2 g, 10 mmol) were slowly added at 0° C. After 4 hour agitation of the mixture at room temperature, solvent was removed under heating for 30 min. Next, dry tetrahydrofuran (20 ml) was put into the reaction vessel and further methyl iodide (12.7 g, 90 mmol) was slowly added. After 12 hour agitation, the reaction mixture was treated by a method similar to the one in the above Examples to obtain (Z)-1,1,1-trifluoro-4-phenyl-3-pentene-2-ol (b.p.: 84°-86° C./2 mmHg) at a yield of 63%. The above product gave the following analytical data:

Aufarbeitung

  1. customat 0° C.
  2. customsolvent was removed
  3. temperatureunder heating for 30 min
  4. additionwas slowly added
  5. waitAfter 12 hour agitation

Quellen und Nachweise

ORD-Eintrag
ord-c7b863e996644d2aa218b8222f6844f3
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04532020

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