4-Ethynyl-1,2-dimethoxybenzene → 1-[-4-(3,4-Dimethoxy-phenylethynyl)-3-methoxy-phenyl]-ethanone

HRID 451261Notes

Reaction equation

HRID 451261 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](OS(C2C=CC(C)=CC=2)(=O)=O)=[C:6]([O:21][CH3:22])[CH:5]=1)(=[O:3])[CH3:2].[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)#[CH:24]>C(Cl)Cl>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([C:23]#[C:24][C:7]2[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]=2[O:21][CH3:22])[CH:30]=[CH:29][C:28]=1[O:31][CH3:32]

Participants

4

Reactant 2

HCID 36164214-Ethynyl-1,2-dimethoxybenzeneHCID 29800848Toluene-4-sulfonic acid 4-acetyl-2-methoxy-phenyl ester

Product 1

HCID 252216081-[-4-(3,4-Dimethoxy-phenylethynyl)-3-methoxy-phenyl]-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 4-acetyl-2-methoxy-phenyl ester and 4-ethynyl-1,2-dimethoxy-benzene following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: DCM; yield (120 mg, 77%); 1H NMR δ (CDCl3): 7.55 (d, J=8.26 Hz, 1H), 7.53-7.48 (m, 2H), 7.18 (dd, J=8.25 Hz, J=2.30 Hz, 1H), 7.07 (m, 1H), 6.84 (d, J=8.24 Hz, 1H), 3.98 (s, 3H), 3.91 (s, 6H), 2.61 (s, 3H); LCMS m/z: 310.

Workup

  1. customyield (120 mg, 77%)

Sources & evidence

ORD record
ord-c15fbbde3b304818bbe571bb3cd6bbf2
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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