1-Ethynyl-2-methoxybenzene → 5-(2-Methoxy-phenyl)-pent-2-en-4-ynoic acid ethyl ester
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10])#[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][CH:6]=[CH:5][C:4]=1[O:9][CH3:10])[CH3:12]Participants
3
Procedure
The general procedure was used to convert 1-Ethynyl-2-methoxy-benzene 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 (480 mg, 98% yield). 1H NMR (400 MHz, CDCl3) δ 7.52-7.50 (dd, J=7.5, 1.7, 1H), 7.33-7.29 (m, 1H), 6.93-6.89 (dt, J=7.6, 0.9, 1H), 6.88-6.86 (d, J=8.3, 1H), 6.42-6.39 (d, J=11.4, 1H), 6.11-6.08 (d, J=11.4, 1H), 4.28-4.22 (q, J=7.1, 2H), 3.88 (s, 3H), 1.33-1.29 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 164.86, 160.32, 134.25, 130.84, 127.67, 123.10, 120.54, 111.96, 110.73, 97.93, 90.45, 60.32, 55.81, 14.28. Anal. Calcd. for C14H14O3: C, 73.03; H, 6.13; Found C, 73.08; H, 6.19.
Sources & evidence
- ORD record
- ord-b09afcc73437458b97eadfa3c475a07a
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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