Tetrahydrofuran → 4-Methoxy-1-[2-(4-methoxyphenyl)vinyl]-2-nitrobenzene

HRID 1950125Notes

Reaction equation

HRID 1950125 reaction equation
I[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.C([Sn](CCCC)(CCCC)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26])CCC.O1CCCC1>CN1CCCC1=O.S1C=CC=C1C([O-])=O.[Cu+]>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=2)=[C:18]([N+:25]([O-:27])=[O:26])[CH:19]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23087474Tributyl(4-methoxy-2-nitrophenyl)tinHCID 572427761-(2-Iodovinyl)-4-methoxybenzene

Product 1

HCID 666267834-Methoxy-1-[2-(4-methoxyphenyl)vinyl]-2-nitrobenzeneYield 72.8%

Reagents, catalysts & solvents 2

HCID 11194830Cuprous 2-thiophenecarboxylateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

By referring to the synthetic method of J. Org. Chem., 1997, 62, 199, to a solution of lithium acetate (280 mg) in water (3 ml) was added acetonitrile (90 ml), the solution was stirred at room temperature, then 4-methoxycinnamic acid (7.5 g), N-iodosuccinimide (10 g) were sequentially added thereto, the solution was stirred for 2 hours at room temperature, and then neutralized with a saturated aqueous solution of sodium bicarbonate. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide 1-(2-iodovinyl)-4-methoxybenzene (8.0 g). By referring to the synthetic method of J. Am. Chem. Soc., 1996, 118, 2748, to a solution of 1-(2-iodovinyl)-4-methoxybenzene (7.1 g) and tributyl(4-methoxy-2-nitrophenyl)tin (10 g) in 1-methyl-2-pyrrolidone (100 ml) was added copper(I) thiophene-2-carboxylate (6.6 g) on an ice bath under a nitrogen atmosphere, and the solution was stirred for 25 minutes at room temperature. Tetrahydrofuran was added thereto, the solution was stirred, then filtered through alumina, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (4.7 g).

Workup

  1. stirringthe solution was stirred
  2. filtrationfiltered through alumina
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-a0d68aca46ce43d8a0c17c8cd291a07b
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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