Methyl 4-ethynylbenzoate → 4-(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][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1.[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][C:7]([C:10]#[C:11][CH:18]=[CH:17][C:16]([O:15][CH2:13][CH3:14])=[O:20])=[CH:6][CH:5]=1Participants
3
Procedure
The general procedure was used to convert 4-Ethynyl-benzoic acid methyl ester 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 solid (450 mg, 88% yield). 1H NMR (400 MHz, CDCl3) δ 8.01-7.99 (d, J=8.5, 2H), 7.59-7.57 (d, J=8.5, 2H), 6.37-6.34 (d, J=11.4, 1H), 6.20-6.17 (d, J=11.4, 1H), 4.29-4.23 (q, J=7.1, 2H), 3.91 (s, 3H), 1.34-1.30 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 166.36, 164.60, 131.91, 130.31, 129.52, 129.37, 127.29, 122.25, 99.73, 88.79, 60.55, 52.24, 14.30. Anal. Calcd. for C15H14O4: C, 69.76; H, 5.46; Found C, 69.90; H, 5.55. m.p.: 49.0°-51.0° C.
Sources & evidence
- ORD record
- ord-c1ebd26157e24856a298247d8dc09d81
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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