Phenylacetylene → (Dec-3-en-1-yn-1-yl)benzene

HRID 1452813Notes

Reaction equation

I/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:10]1([C:16]#[CH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[C:17][CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 10944471cis-1-Iodo-1-octene

Product 1

HCID 54043394(Dec-3-en-1-yn-1-yl)benzene

Procedure

The modified procedure was used to convert (Z)-1-Iodo-oct-1-ene and phenyl acetylene to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a colorless oil (420 mg, 98% yield). 1H NMR (400 MHz, CDCl3) δ 7.44-7.41 (m, 2H), 7.29-7.27 (m, 3H), 5.99-5.92 (m, 1H), 5.67-5.65 (d, J=10.7, 1H), 2.42-2.36 (m, 2H), 1.46-1.43 (m, 2H), 1.37-1.29 (m, 6H), 0.89-0.86 (m, 3H). 13C NMR (100 MHz, CDCl3) δ 144.36, 131.42, 128.30, 127.96, 123.82, 109.06, 93.46, 86.57, 31.76, 30.45, 28.96, 28.91, 22.70, 14.16. Anal. Calcd. for C16H20: C, 90.51; H, 9.49; Found C, 90.24; H, 9.47.

Sources & evidence

ORD record: ord-ea00e1cc5742430e9b3cd6aee196ff18
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473797B2

Reaction notes

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