Phenylacetylene → HCID 15352365, compound

HRID 1452814Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH:11]=1>>[C:1]1([C:7]#[C:8][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 44248463HCID 44248463, compound

Product 1

HCID 15352365HCID 15352365, compound

Procedure

The modified procedure was used to convert phenylacetylene and 1,2-dihydro-4-iodonaphthalene to the title product in 24 hours. Purification by flash chromatography (20% CH2Cl2 in hexanes) gave the analytically pure product as a light yellow oil (360 mg, 78% yield). 1H NMR (400 MHz, CDCl3) δ 7.68 (d, J=7.58, 1H), 7.52 (m, 2H), 7.31 (m, 3H), 7.25 (m, 1H), 7.18 (t, 1H), 7.13 (d, J=7.33, 1H), 6.54 (t, 1H), 2.80 (t, 2H), 2.42, (m, 2H). 13C NMR (100 MHz, CDCl3) δ 135.49, 135.05, 132.64, 131.54, 128.29, 128.07, 127.66, 127.39, 126.62, 125.05, 123.43, 121.72, 90.28, 87.29, 27.14, 23.69. Anal. Calc'd. for C18H14: C, 93.87; H, 6.13; Found C, 93.79; H, 6.36.

Sources & evidence

ORD record: ord-a61d4b3aae0242f89d232e888de51e3e
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473797B2

Reaction notes

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