ethyl (2Z)-3-iodoprop-2-enoate → 5-(4-Methylsulfanyl-phenyl)-pent-2-en-4-ynoic acid ethyl ester
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9][CH3:10])=[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:8]=[CH:7][C:6]([S:9][CH3:10])=[CH:5][CH:4]=1)[CH3:12]Participants
3
Procedure
The general procedure was used to convert 1-Ethynyl-4-methylsulfanyl-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 (450 mg, 91% yield). 1H NMR (400 MHz, CDCl3) δ 7.44-7.42 (d, J=8.5, 2H), 7.18-7.16 (d, J=8.5, 2H), 6.35-6.32 (d, J=11.4, 1H), 6.11-6.09 (d, J=11.4, 1H), 4.28-4.22 (q, J=7.1, 2H), 2.46 (s, 3H), 1.34-1.30 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 164.81, 140.87, 132.33, 127.85, 125.68, 122.81, 118.84, 101.21, 86.77, 60.37, 15.16, 14.32. Anal. Calcd. for C14H14O2S: C, 68.26; H, 5.73; S, 13.02; Found C, 68.50; H, 5.88; S, 13.18.
Sources & evidence
- ORD record
- ord-d452962cb6a24878bf83342120789980
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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