Isoprene → Trimethyl(4-methyl-1,4-cyclohexadienyl)silane

HRID 1361744Notes

Reaction equation

HRID 1361744 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[CH3:6][Si:7]([C:10]#[CH:11])([CH3:9])[CH3:8]>ClCCl.[Zn+2].[I-].[I-].C1(P(CC)C2C=CC=CC=2)C=CC=CC=1>[CH3:6][Si:7]([CH3:9])([CH3:8])[C:10]1[CH2:11][CH:5]=[C:3]([CH3:4])[CH2:2][CH:1]=1

Participants

6

Reactant 2

HCID 6557IsopreneHCID 66111Trimethylsilylacetylene

Product 1

HCID 10057893Trimethyl(4-methyl-1,4-cyclohexadienyl)silaneYield 91.7%

Reagents, catalysts & solvents 3

HCID 69082EthyldiphenylphosphineCatalystHCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
30 °C

Procedure

In a four-necked flask, 1.12 g (5.1 mmol) of CoBr2, 5.43 g (17 mmol) of ZnI2, and 2.24 g (5.6 mmol) of diphenylphosphinoethane were dissolved in 250 ml of dichloromethane, and the solution was stirred for 30 minutes at 30° C. Subsequently, 50 ml (500 mmol) of isoprene, 63.5 ml (450 mmol) of trimethylsilylacetylene, and 1.45 g (5.6 mmol) of Bu4NBH4 were added thereto, and the mixture was allowed to react for one hour at 30° C. After completion of the reaction, dichloromethane was evaporated, and then the residue was distilled under reduced pressure. Thus, 68.6 g of the title compound, trimethyl (4-methyl-1,4-cyclohexadienyl) silane, was obtained at a yield of 91.7% (GC purity 80%).

Workup

  1. customto react for one hour at 30° C
  2. customwas evaporated
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-cfbae19e7385447f98a5e83478b24ce4
Source dataset
uspto-grants-2011_02
Patent number
US07880025B2

Reaction notes

Loading…