Isobutyl chloride → (Z)-1,1,1-trifluoro-4-phenyl-3-butene-2-ol

HRID 371367

Reaction equation

HRID 371367 reaction equation
C([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>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]=[CH:17]\[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 10554Isobutyl chlorideHCID 5462224MagnesiumHCID 114129783-Butyn-2-ol, 1,1,1-trifluoro-4-phenyl-HCID 178418368HCID 178418368, compound

Product 1

HCID 12755329(Z)-1,1,1-trifluoro-4-phenyl-3-butene-2-olYield 53%

Reagents, catalysts & solvents 2

HCID 416358Bis(cyclopentadienyl)titanium(IV) chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

In an isobutylmagnesium chloride solution that was prepared by reacting isobutyl chloride (2.34 g, 25 mmol) and magnesium (0.66 g, 27 mmol) in dry ether (30 ml) at 0° C., dichlorobis(π-cyclopentadienyl)titanium (0.14 g, 0.56 mmol) and 1,1,1,-trifluoro-4-phenyl-3-butyne-2-ol (2g, 10 mmol) were slowly added at 0° C. After 1 hour agitation at the same temperature, 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-butene-2-ol (b.p.: 78°-80° C./3 mmHg) at a yield of 53%. The above product gave the following analytical data:

Workup

  1. customat 0° C.

Sources & evidence

ORD record
ord-dc9653106666434a8f997356c245e2c9
Source dataset
uspto-grants-1985_07
Patent number
US04532020

Linked notes

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