1,4-Diethynylbenzene → 5-[4-(4-Ethoxycarbonyl-but-3-en-1-ynyl)-phenyl]-pent-2-en-4-ynoic acid ethyl ester
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1)#[CH:2].[CH2:11]([O:13][C:14](=[O:18])/[CH:15]=[CH:16]\I)[CH3:12]>>[CH2:11]([O:13][C:14](=[O:18])[CH:15]=[CH:16][C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH:16]=[CH:15][C:14]([O:13][CH2:11][CH3:12])=[O:18])=[CH:5][CH:4]=1)[CH3:12]Participants
3
Procedure
The general procedure was used to convert 1,4-Diethynyl-benzene and (Z)-ethyl-3-iodoacrylate to the title product in 12 hours. Purification by flash chromatography (10% ethyl acetate in hexane as the eluent) gave the analytically pure product as a light yellow solid (560 mg, 87% yield). 1H NMR (400 MHz, CDCl3) δ 7.50 (s, 4H), 6.37-6.34 (d, J=11.4, 2H), 6.17-6.14 (d, J=11.4, 2H), 4.28-4.23 (q, J=7.1, 4H), 1.34-1.30 (t, J=7.1, 6H). 13C NMR (100 MHz, CDCl3) δ 164.57, 131.88, 128.72, 123.31, 122.34, 100.27, 88.36, 60.39, 14.21. Anal. Calcd. for C20H18O4: C, 74.52; H, 5.63; Found C, 74.33; H, 5.71. m.p.: 73.0°-74.0° C.
Sources & evidence
- ORD record
- ord-b165804e0ef84b0aa9a98e04efd8b27f
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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