Toluene → 1-(4-Methoxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene

HRID 2121311Notes

Reaction equation

HRID 2121311 reaction equation
[O-]CC.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1.C1(C)C=CC=CC=1.Br[C:23]1[S:24][C:25]([C:28]#[N:29])=[CH:26][CH:27]=1>O>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:23]2[S:24][C:25]([C:28]#[N:29])=[CH:26][CH:27]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 2510201-Ethynyl-4-methoxybenzeneHCID 2723922Sodium ethoxideHCID 35950595-Bromothiophene-2-carbonitrile

Product 1

HCID 234322581-(4-Methoxyphenyl)-2-(2-cyanothiophen-5-yl)acetyleneYield 33.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of sodium ethoxide (0.7 g), 1-(4-methoxyphenyl)acetylene (0.5 g), and toluene (40 cm3) is stirred for 2 h, 2-bromo-5-cyanothiophene (0.7 g), is added and the resultant mixture heated under reflux for 3 h. The reaction mixture is poured into water (500 cm3) and the organic layer separated off. The aqueous layer is then extracted with toluene (2×50 cm3). The combined organic layers are washed with water (2×200 cm3), dried (MgSO4), filtered and then evaporated down. The residue is purified by column chromatography on silica gel using a 95:5 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield 0.3 g of 1-(4-methoxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene.

Workup

  1. temperatureunder reflux for 3 h
  2. customthe organic layer separated off
  3. extractionThe aqueous layer is then extracted with toluene (2×50 cm3)
  4. washThe combined organic layers are washed with water (2×200 cm3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated down
  8. customThe residue is purified by column chromatography on silica gel using a 95:5 hexane/ethyl acetate mixture as eluent
  9. customrecrystallisation from ethanol

Sources & evidence

ORD record
ord-cf7438c8b69c4f7abc6f247692f84bea
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

Loading…