4-Methoxy cinnamic acid → 1-(2-Iodovinyl)-4-methoxybenzene

HRID 1433938

反応式

HRID 1433938 の反応式
C([O-])(=O)C.[Li+].[CH3:6][O:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12]=[CH:13]C(O)=O)=[CH:10][CH:9]=1.[I:19]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O.C(#N)C>[I:19][CH:13]=[CH:12][C:11]1[CH:17]=[CH:18][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1

参加物

7

反応物 4

HCID 132454-Methoxy cinnamic acidHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 3474584Lithium acetate

生成物 1

HCID 572427761-(2-Iodovinyl)-4-methoxybenzene収率 73.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  1. stirringthe solution was stirred for 2 hours at room temperature
  2. extractionThe solution was extracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

出典と根拠

ORDレコード
ord-ab3871690d7d45bd83602221508ca57e
出典データセット
uspto-grants-2009_11
特許番号
US07612114B2

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