Phenylacetylene → HCID 11321375, compound

HRID 1452809Notes

Reaction equation

HRID 1452809 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11](=[O:15])/[CH:12]=[CH:13]\I>>[C:1]1([C:7]#[C:8]/[CH:13]=[CH:12]\[C:11]([O:10][CH3:9])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 5463377(Z)-3-Iodopropenoic acid methyl ester

Product 1

HCID 11321375HCID 11321375, compound

Procedure

The general procedure was used to convert phenylacetylene and (Z)-methyl-3-iodoacrylate to the title product. Purification by flash chromatography (15% ethyl acetate in hexanes as the eluent) gave the analytically pure product as a light yellow oil (336 mg, 90% yield). 1H NMR (400 MHz, CDCl3) δ 7.54 (m, 2H), 7.35 (m, 3H), 6.36 (d, J=11.39, 1H), 6.14 (d, J=11.41, 1H), 3.80 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 165.25, 132.16, 129.28, 128.42, 127.79, 123.22, 122.63, 101.45, 86.37, 51.55. Anal. Calc'd. for C12H10O2: C, 77.40; H, 5.41; Found C, 77.41; H, 5.35.

Sources & evidence

ORD record
ord-c414cba671a1454481c4e83e1e1e138e
Source dataset
uspto-grants-2009_01
Patent number
US07473797B2

Reaction notes

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