Triethylsilane → (E)-alpha-triethylsilyl-beta-methylstyrene

HRID 1646843Notes

Reaction equation

HRID 1646843 reaction equation
C1(C#CC)C=CC=CC=1.C([SiH](CC)CC)C.C([Si](CC)(CC)/C(/C)=C\C1C=CC=CC=1)C.C([Si](CC)(CC)/C(/C)=C/C1C=CC=CC=1)C.[CH2:49]([Si:51]([CH2:63][CH3:64])([CH2:61][CH3:62])/[C:52](/[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[CH:53]\[CH3:54])[CH3:50]>[Rh](Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:61]([Si:51]([CH2:49][CH3:50])([CH2:63][CH3:64])/[C:52](/[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[CH:53]/[CH3:54])[CH3:62]

Participants

7

Reactant 5

HCID 12052TriethylsilaneHCID 69601MethylphenylacetyleneHCID 11817139(E)-beta-triethylsilyl-beta-methylstyreneHCID 14920929(Z)-beta-triethylsilyl-beta-methylstyreneHCID 14920931(Z)-alpha-triethylsilyl-beta-methylstyrene

Product 1

HCID 14920930(E)-alpha-triethylsilyl-beta-methylstyreneYield 4%

Reagents, catalysts & solvents 1

HCID 157991709Trichlororhodium;tris(triphenylphosphane)Catalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 0.125 ml (1.0 mmol) of 1-phenylpropyne, 0.192 ml (1.2 mmol) of triethylsilane, and 9.9 mg (0.01 mmol) of chlorodium tris(triphenylphosphine) rhodium chloride was heated in a sealed tube at 100° C. for 16 hours while being stirred. GLC analysis of the reaction mixture revealed that (Z)-β-triethylsilyl-β-methylstyrene, (E)-β-triethylsilyl-β-methylstyrene, (Z)-α-triethylsilyl-β-methylstyrene, and (E)-α-triethylsilyl-β-methylstyrene were produced in a yield of 4%, 33%, 7%, and 56%, respectively.

Sources & evidence

ORD record
ord-241c10fcd7f447d7ba8b322440f26b2c
Source dataset
uspto-grants-1993_01
Patent number
US05182246

Reaction notes

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