Phenylacetylene → HCID 25222060, compound

HRID 1967199Notes

Reaction equation

HRID 1967199 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1OS(C1C=CC(C)=CC=1)(=O)=O)=[O:4].[C:21]1([C:27]#[CH:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCCCCCC.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:28]#[C:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:4]

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 2808173HCID 2808173, compound

Product 1

HCID 25222060HCID 25222060, compound

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from 3-(toluene-4-sulfonyloxy)-thiophene-2-carboxylic acid methyl ester and phenylacetylene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 1:1; yield (91 mg, 75%); 1H NMR δ (CDCl3): 7.53 (m, 2H), 7.39 (d, J=5.02 Hz, 1H), 7.3 (m, 3H), 7.12 (d, J=5.10 Hz, 1H), 3.82 (s, 3H); LCMS m/z: 242.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (91 mg, 75%)

Sources & evidence

ORD record
ord-0b00ab370a1345159c4e39d182f611b3
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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