Phenylacetylene → HCID 11119343, compound

HRID 1452810Notes

Reaction equation

HRID 1452810 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I/[C:10](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:11]\[C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[C:17]1(/[C:10](/[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 11130420HCID 11130420, compound

Product 1

HCID 11119343HCID 11119343, compound

Procedure

The general procedure was used to convert phenylacetylene and (Z)-ethyl 3-iodo-3-phenylacrylate to the title product. Purification by flash chromatography (5% ethyl acetate in hexanes as the eluent) gave the analytically pure product as a light yellow oil (530 mg, 96% yield). 1H NMR (400 MHz, CDCl3) δ 7.78 (m, 2H), 7.63 (m, 2H), 7.38 (m, 6H), 6.59 (s, 1H), 2.06 (q, 2H), 1.35 (t, 3H). 13C NMR (100 MHz, CDCl3) δ 165.12, 136.92, 136.08, 131.85, 129.66, 128.99, 128.42, 128.18, 126.96, 122.54, 122.48, 101.88, 86.68, 60.16, 14.17. Anal. Calc'd. for C19H16O2: C, 82.58; H, 5.84; Found C,

Sources & evidence

ORD record
ord-c71a3a3316004c0494cbfb120d3f1a79
Source dataset
uspto-grants-2009_01
Patent number
US07473797B2

Reaction notes

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