ChemicalBook CAS DataBase List 1-Ethyl-4-[(4-Methoxyphenyl)ethynyl]benzene

1-Ethyl-4-[(4-Methoxyphenyl)ethynyl]benzene synthesis

7synthesis methods

Product Name:1-Ethyl-4-[(4-Methoxyphenyl)ethynyl]benzene
CAS Number:63221-88-5
Molecular formula:C17H16O
Molecular Weight:236.31

40307-11-7 Synthesis

40307-11-7
174 suppliers
$6.00/1g

5720-07-0 Synthesis

5720-07-0
455 suppliers
$6.00/5g

1-Ethyl-4-[(4-Methoxyphenyl)ethynyl]benzene

63221-88-5
65 suppliers
$44.00/1g

Yield: 75%

Reaction Conditions:

with C₂₆H₂₂N₃OPPdS;potassium acetate;silver(l) oxide in dichloromethane at 35; for 24 h;Schlenk technique;Inert atmosphere;

Steps:

4.2.21. 1-Ethyl-4-((4-methoxyphenyl)ethynyl)benzene
A mixture of arylboronic acid (0.5 mmol), terminal alkyne oralkynyl carboxylic acid (0.6 mmol), DCM (2 mL), catalyst 3 (2 mol %),Ag2O (1.0 mmol) and KOAc (1.0 mmol) in a Schlenk tube was stirredunder an argon atmosphere at 35 Cfor24h.TheexcessDCMwasthen removed by rotary evaporation and the residue was directlypuried by ash column chromatography (petroleum ether or pe-troleum ether/ethyl acetate) to afford the corresponding couplingproducts. 4.2.21. 1-Ethyl-4-((4-methoxyphenyl)ethynyl)benzene (Fig. 4, entry6) (89 mg, 75% yield). Yellow oil;1H NMR (400 MHz, CDCl3) d 7.49(t, J8.8 Hz, 4H), 7.20 (d, J7.6 Hz, 2H), 6.90 (d, J8.6 Hz, 2H), 3.82(s, 3H), 2.68 (q, J7.4 Hz, 2H), 1.27 (t, J7.6 Hz, 3H).13C NMR(100 MHz, CDCl3) d 159.4, 144.3, 132.9, 131.4, 127.9, 120.7, 115.5,113.9, 88.7, 88.2, 55.2, 28.8, 15.4. MS ESI(m/z): [MH]calcd for[C17H17O]requires 237.1, found 237.1

References:

Lu, Linhua;Chellan, Prinessa;Smith, Gregory S.;Zhang, Xiang;Yan, Hong;Mao, Jincheng [Tetrahedron,2014,vol. 70,# 35,p. 5980 - 5985]

25309-64-2 Synthesis