Methyl 2-ethynylbenzoate → 2-(4-Ethoxycarbonyl-but-3-en-1-ynyl)-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11].[CH2:13]([O:15][C:16](=[O:20])/[CH:17]=[CH:18]\I)[CH3:14]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][CH:18]=[CH:17][C:16]([O:15][CH2:13][CH3:14])=[O:20]Participants
Procedure
The general procedure was used to convert 2-Ethynyl-benzoic acid methyl ester and (Z)-ethyl-3-iodoacrylate to the title product. Purification by flash chromatography (20% ethyl acetate in hexane as the eluent) gave the analytically pure product as a light yellow oil (410 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ 7.96-7.95 (d, J=7.8, 1H), 7.70-7.68 (d, J=8.2, 1H), 7.50-7.46 (t, J=7.5, 1H), 7.37-7.41 (t, J=7.7, 1H), 6.46-6.43 (d, J=11.4, 1H), 6.18-6.15 (d, J=11.4, 1H), 4.27-4.21 (q, J=7.1, 2H), 3.92 (s, 3H), 1.31-1.27 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 166.31, 164.65, 134.69, 131.79, 131.74, 130.42, 128.73, 128.70, 123.23, 122.91, 99.64, 90.93, 60.40, 52.23, 14.27. Anal. Calcd. for C15H14O4: C, 69.76; H, 5.46; Found C, 69.93; H, 5.59.
Sources & evidence
- ORD record
- ord-1e741d9d6eae4199ba04739313b73611
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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