Lithium iodide → (1-Heptenyl)di(isopropyl)silane

HRID 984504Notes

Reaction equation

HRID 984504 reaction equation
I/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[I-].[Li+].C([Li])CCC.Cl[SiH:17]([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19]>>[CH:2]([SiH:17]([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 66321Lithium iodideHCID 2758383Chlorodi(isopropyl)silaneHCID 10966141(Z)-1-iodo-1-hepteneHCID 178418339Butyllithium

Product 1

HCID 123241814(1-Heptenyl)di(isopropyl)silaneYield 95%

Procedure

To investigate the influence of the non-transferable groups on the silicon atom (and illustrate an alternative entry to the silanol precurors) di(isopropyl(silanols (E)-52 and (Z)-52 (Scheme 6) were prepared. Catalytic (H2PtCl6) hydrosilylation of 1-heptyne with chlorodi(isopropyl)silane followed by alkaline hydrolysis provided (E)-52 in 78% yield (25). The stereoisomer (Z)-52, was produced by a high yielding four-step synthesis starting from (Z)-1-iodo-1-heptene. Lithium-iodide exchange with n-butyllithium, followed by the addition of chlorodi(isopropyl)silane formed the intermediate (1-heptenyl)di(isopropyl)silane in 95% yield. Oxidation with chlorine (0.9 M solution in CCl4), followed by mild hydrolysis produced (Z)-52 in 90% yield over two steps.

Workup

  1. customThe stereoisomer (Z)-52, was produced by
  2. customa high yielding
  3. customfour-step synthesis

Sources & evidence

ORD record
ord-3be56a679d8949209a55e6d85af0b57c
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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