Potassium Fluoride → 2-Ethynyl-5-hexylthiophene

HRID 1958757Notes

Reaction equation

HRID 1958757 reaction equation
[CH2:1]([C:7]1[S:11][C:10]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F-].[K+]>>[C:12]([C:10]1[S:11][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=1)#[CH:13]

Participants

3

Reactant 2

HCID 522689Potassium FluorideHCID 68743804[(5-Hexylthiophen-2-yl)ethynyl](trimethyl)silane

Product 1

HCID 235220852-Ethynyl-5-hexylthiophene

Procedure

According to the method of S117b, ((5-hexylthiophen-2-yl)ethynyl)trimethylsilane (1 g, 3.7 mmol) was reacted with potassium fluoride (429 mg, 7.4 mmol) to give the title compound as a yellow oil following silica gel purification (hexane) (500 mg, 70%). 1H NMR (400 MHz, CDCl3) δ 7.10 (d, 1H, J=3.6 Hz), 6.64 (d, 1H, J=3.6 Hz), 2.78 (t, 2H, J=7.2 Hz) 1.68-1.55 (m, 2H), 1.36-1.28 (m, 6H), 0.89 (t, 3H, J=6.4 Hz).

Sources & evidence

ORD record
ord-8318a5b0362b49ee8ad66d5689a14a37
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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