1-Octyne → (Z)-ethyl undec-2-en-4-ynoate
Reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:9]([O:11][C:12](=[O:16])/[CH:13]=[CH:14]\I)[CH3:10]>>[C:12]([O:11][CH2:9][CH3:10])(=[O:16])/[CH:13]=[CH:14]\[C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
3
Procedure
The general procedure was used to convert n-octyne and (Z)-ethyl-3-iodoacrylate to the title product. Purification by flash chromatography (5% ethyl acetate in hexane as the eluent) gave the analytically pure product as a light yellow oil (401 mg, 96% yield). 1H NMR (400 MHz, CDCl3) δ 6.13 (dt, J=10.82, 1H), 6.02 (d, J=10.96, 1H), 4.21 (q, 2H), 2.44 (m, 2H), 1.58 (p, 2H), 1.42 (m, 2H), 1.30-1.28 (m, 7H), 0.89 (t, 3H). 13C NMR (100 MHz, CDCl3) δ 164.87, 127.34, 123.89, 104.17, 77.66, 60.18, 31.30, 28.60, 28.36, 22.49, 20.07, 14.21, 13.99. Anal. Calcd. for C13H20O2: C, 74.96; H, 9.68; Found C, 74.96; H, 9.56.
Sources & evidence
- ORD record
- ord-a78c5163cc504660a0c52d4d04d46b06
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473797B2
Reaction notes
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