Phenylacetylene → HCID 11031167, compound

HRID 1452811Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[C:1]1([C:7]#[C:8]/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 11118103(1E)-1-Iodo-1-octene

Product 1

HCID 11031167HCID 11031167, compound

Procedure

The general procedure was used to convert phenylacetylene and (E)-1-iodooctene to the title product in 24 hours. Purification by flash chromatography (light petroleum ether as eluent) gave the analytically pure product as a clear oil (423 mg, 99% yield). 1H NMR (400 MHz, CDCl3) δ 7.40 (m, 2H), 7.28 (m, 3H), 6.24 (m, 1H), 5.68 (d, J=15.84, 1H), 2.15 (q, 2H), 1.41-1.28 (m, 8H), 0.89 (t, 3H). 13C NMR (100 MHz, CDCl3) δ 145.08, 131.24, 128.07, 127.67, 123.49, 109.32, 88.23, 87.68, 33.08, 31.52, 28.66, 28.59, 22.45, 13.94. Anal. Calc'd. for C16H20: C, 90.51; H, 9.49; Found C, 90.65; H, 9.58.

Sources & evidence

ORD record: ord-f4f09e3037454c68bdcbd504d2ec4bca
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473797B2

Reaction notes

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