ethyl (2Z)-3-iodoprop-2-enoate → 5-(4-Cyano-phenyl)-pent-2-en-4-ynoic acid ethyl ester
Reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[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:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)[CH3:12]Participants
3
Procedure
The general procedure was used to convert 4-Ethynyl-Bezonitrile 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 solid (380 mg, 85% yield). 1H NMR (400 MHz, CDCl3) δ 7.64-7.59 (m, J=8.5, 4H), 6.37-6.34 (d, J=11.3, 1H), 6.24-6.21 (d, J=11.3, 1H), 4.28-4.23 (q, J=7.1, 2H), 1.34-1.30 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 164.40, 132.39, 132.03, 130.08, 127.49, 121.74, 118.25, 112.37, 98.34, 89.94, 60.57, 14.23. Anal. Calcd. for C14H11NO2: C, 74.65; H, 4.92, N, 6.22; Found C, 74.45; H, 4.84, N, 6.06. m.p.: 69.5°-71.5° C.
Sources & evidence
- ORD record
- ord-7d617ce960754f56b9e57061f687ce9f
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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