1-Ethynyl-4-methoxybenzene → HCID 25221834, compound

HRID 451281Notes

Reaction equation

HRID 451281 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](OS(C1C=CC=CC=1)(=O)=O)[CH:7]=[CH:6]2)#[N:2].[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)#[CH:24]>CCCCCCC.CCOC(C)=O>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]#[C:24][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH:4]=[C:3]([C:1]#[N:2])[CH:12]=[CH:11]3)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 86646626HCID 86646626, compound

Product 1

HCID 25221834HCID 25221834, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from benzenesulfonic acid 6-cyano-naphthalen-2-yl ester and 1-ethynyl-4-methoxy-benzene following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 95:5; yield (140 mg, 98%); 1H NMR δ (CDCl3): 8.20 (s, 1H), 8.06 (s, 1H), 7.88 (t, J=7.81 Hz, 2H), 7.71-7.59 (dm, 2H), 6.92 (m, 2H), 3.83 (s, 3H); LCMS m/z: 283.

Workup

  1. customyield (140 mg, 98%)

Sources & evidence

ORD record
ord-93a6d63da4ee4c5fb071555e3da7d430
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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