1-Ethynyl-4-methoxybenzene → HCID 25222063, compound

HRID 1967200Notes

Reaction equation

HRID 1967200 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[C:6]([CH3:18])[C:7]=1OS(C1C=CC=CC=1)(=O)=O)#[N:2].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)#[CH:20]>CCCCCCC.CCOC(C)=O>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]#[C:20][C:7]2[C:6]([CH3:18])=[CH:5][S:4][C:3]=2[C:1]#[N:2])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 86646618HCID 86646618, compound

Product 1

HCID 25222063HCID 25222063, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from benzenesulfonic acid 2-cyano-4-methyl-thiophen-3-yl ester and 1-ethynyl-4-methoxy-benzene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 9:1; yield (110 mg, 87%); 1H NMR δ (CDCl3): 7.51 (d, J=8.52 Hz, 2H), 6.88 (d, J=8.60 Hz, 2H), 6.81 (s, 1H), 3.84 (s, 3H), 2.51 (s, 3H); LCMS m/z: 253.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (110 mg, 87%)

Sources & evidence

ORD record
ord-54b746127803497db3303e051a402b8c
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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