5-Hexynenitrile → 4-(5-Cyano-pent-1-ynyl)-3-methoxy-benzonitrile

HRID 451278Notes

Reaction equation

HRID 451278 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C2C=CC=CC=2)(=O)=O)=[C:5]([O:19][CH3:20])[CH:4]=1)#[N:2].[C:21](#[N:27])[CH2:22][CH2:23][CH2:24][C:25]#[CH:26]>CCCCCCC.CCOC(C)=O>[C:21]([CH2:22][CH2:23][CH2:24][C:25]#[C:26][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[O:19][CH3:20])#[N:27]

Participants

4

Reactant 2

HCID 1398525-HexynenitrileHCID 24235536Benzenesulfonic acid 4-cyano-2-methoxy-phenyl ester

Product 1

HCID 252218314-(5-Cyano-pent-1-ynyl)-3-methoxy-benzonitrile

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from benzenesulfonic acid 4-cyano-2-methoxy-phenyl ester and 5-hexynenitrile following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 8:2; yield (70 mg, 62%); 1H NMR δ (CDCl3): 7.52 (d, J=8.34 Hz, 1H), 7.21 (d, J=8.22 Hz, 1H), 7.11 (s, 1H), 3.81 (s, 3H), 2.69 (t, J=7.25 Hz, 2H), 2.58 (t, J=7.22 Hz, 2H), 1.99 (p, J=7.12 Hz, 2H); LCMS m/z: 224.

Workup

  1. customyield (70 mg, 62%)

Sources & evidence

ORD record
ord-0b998119744943cb85e97391c0708c6c
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

Loading…