Ethyltrimethylsilane → ((3-(Hexyloxy)phenyl)ethynyl)trimethylsilane

HRID 1958760Notes

Reaction equation

HRID 1958760 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]C)[CH:3]=1.[CH3:16][Si:17]([CH2:20][CH3:21])([CH3:19])[CH3:18]>>[CH2:9]([O:8][C:4]1[CH:3]=[C:2]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[CH:7]=[CH:6][CH:5]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 137936EthyltrimethylsilaneHCID 431294771-Bromo-3-(heptyloxy)benzene

Product 1

HCID 68743503((3-(Hexyloxy)phenyl)ethynyl)trimethylsilaneYield 55%

Procedure

According to the method described in Example S117a, 1-bromo-3-(heptyloxy)benzene (1 g, 4 mmol) was reacted with trimethylsilylethane (0.43 g, 4.4 mmol) to give the title compound as a yellow oil (575 mg, 55%). 1H NMR (400 MHz, CDCl3) δ 7.19 (t, 1H, J=7.6 Hz), 7.05 (d, 1H, J=7.2 Hz), 6.99 (s, 1H), 6.87 (d, 1H, J=7.0 Hz), 3.94 (t, 2H, J=6.8 Hz), 1.79-1.75 (m, 2H), 1.47-1.30 (m, 6H), 0.91 (t, 3H, J=6.8 Hz), 0.26 (s, 9H).

Sources & evidence

ORD record
ord-1826ae534ca54637b4b9ca3386c0d43a
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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