1-Octyne → 4-hex-1-ynylbenzonitrile

HRID 451268Notes

Reaction equation

HRID 451268 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[CH:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25]CC>CCCCCCC.CCOC(C)=O>[C:20]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)#[C:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 123701-OctyneHCID 11482693Benzonitrile, 4-[[(4-methylphenyl)sulfonyl]oxy]-

Product 1

HCID 27793604-hex-1-ynylbenzonitrile

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 4-cyano-phenyl ester and 1-octyne following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 9:1; yield (100 mg, 95%); 1H NMR δ (CDCl3): 7.56 (d, J=8.61 Hz, 2H), 7.46 (d, J=8.62 Hz, 2H), 2.43 (t, J=7.44 Hz, 2H), 1.6 (p, J=7.37 Hz, 2H), 1.5-1.4 (m, 2H), 1.38-1.26 (m, 4H), 0.92 (t, J=7.36 Hz, 3H); LCMS m/z: 211.

Workup

  1. customyield (100 mg, 95%)

Sources & evidence

ORD record
ord-c9830f780daf4656896f155706249630
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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