Ethyltrimethylsilane → [(5-Hexylthiophen-2-yl)ethynyl](trimethyl)silane

HRID 1958756Notes

Reaction equation

Br[C:2]1[S:3][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:5][CH:6]=1.[CH3:13][Si:14]([CH2:17][CH3:18])([CH3:16])[CH3:15]>>[CH2:7]([C:4]1[S:3][C:2]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:6][CH:5]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Reactant 2

HCID 137936Ethyltrimethylsilane

HCID 105624182-Bromo-5-hexylthiophene

Product 1

HCID 68743804[(5-Hexylthiophen-2-yl)ethynyl](trimethyl)silaneYield 101.1%

Procedure

According to the method described in S117a, 2-bromo-5-hexylthiophene (1 g, 4 mmol) was reacted with trimethylsilylethane (0.43 g, 4.4 mmol) to give the title compound as a yellow oil (1.07 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.05 (d, 1H, J=3.6 Hz), 6.61 (d, 1H, J=3.6 Hz), 2.77 (t, 2H, J=7.2 Hz) 1.65-1.56 (m, 2H), 1.36-1.30 (m, 6H), 0.89 (t, 3H, J=6.4 Hz), 0.24 (s, 9H).

Sources & evidence

ORD record: ord-e0e5bb213d31495bac77b4fd8a4661e1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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