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

HRID 1361745Notes

Reaction equation

[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[CH:6]([Si:9]([C:16]#[CH:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])([CH3:8])[CH3:7]>[Zn+2].[I-].[I-].C1(P(CC)C2C=CC=CC=2)C=CC=CC=1.ClCCl>[CH:13]([Si:9]([CH:6]([CH3:7])[CH3:8])([CH:10]([CH3:12])[CH3:11])[C:16]1[CH2:17][CH:5]=[C:3]([CH3:4])[CH2:2][CH:1]=1)([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 30 °C

Procedure

In a four-necked flask, 0.27 g (1.2 mmol) of CoBr2, 1.33 g (4.2 mmol) of ZnI2, 0.55 g (1.4 mmol) of diphenylphosphinoethane, and 60 ml of dichloromethane were added, and the mixture was stirred for 30 minutes at 30° C. Subsequently, 12.2 ml (122 mmol) of isoprene, 20 g (110 mmol) of triisopropylsilylacetylene, and 0.35 g (1.4 mmol) of Bu4NBH4 were added thereto, and the mixture was allowed to react for one hour at 30° C. Dichloromethane was evaporated, and then the residue was purified by silica gel flash column chromatography. Thus, 24.6 g of the title compound, triisopropyl(4-methyl-1,4-cyclohexadienyl)silane, was obtained at a yield of 89.7% (GC purity 80%).

Workup

customto react for one hour at 30° C
customDichloromethane was evaporated
customthe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record: ord-bb2c301c7c3f43cfa8e230a5cc4b7f23
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880025B2

Reaction notes

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