ethyl (2Z)-3-iodoprop-2-enoate → 5-(4-Amino-phenyl)-pent-2-en-4-ynoic acid ethyl ester
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)#[CH:2].[CH2:10]([O:12][C:13](=[O:17])/[CH:14]=[CH:15]\I)[CH3:11]>>[CH2:10]([O:12][C:13](=[O:17])[CH:14]=[CH:15][C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)[CH3:11]Participants
3
Procedure
The general procedure was used to convert 4-Ethynyl-phenylamine and (Z)-ethyl-3-iodoacrylate to the title product. Purification by flash chromatography (30% ethyl acetate in hexane as the eluent) gave the analytically pure product as a light yellow oil (350 mg, 90% yield). 1H NMR (400 MHz, CDCl3) δ 7.34-7.32 (d, J=8.4, 2H), 6.60-6.58 (d, J=8.4, 2H), 6.36-6.34 (d, J=11.4, 1H), 6.05-6.02 (d, J=11.4, 1H), 4.28-4.23 (q, J=7.1, 2H), 3.96 (s, 2H), 1.35-1.31 (t, J=7.1, 3H). 13C NMR(100 MHz, CDCl3) δ 165.21, 148.01, 133.78, 125.92, 123.66, 114.54, 111.33, 103.46, 85.59, 60.28, 14.32. Anal. Calcd. for C13H13NO2: C, 72.54; H, 6.09; N, 6.51; Found C, 72.63; H, 6.26; N, 6.32.
Sources & evidence
- ORD record
- ord-5e8da483dd7144d7bcb9c6ebfddbb07a
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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