Thionyl Chloride → 2,4,6,7-Tetramethyl-5-nitro-2,3-dihydro-1-benzofuran-2-carbonyl chloride

HRID 1987770ノート

反応式

HRID 1987770 の反応式
[CH3:1][C:2]1([C:17]([OH:19])=O)[CH2:6][CH:5]2[CH:7]([CH3:16])[C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:12])[C:10]([CH3:11])=[C:4]2[O:3]1.S(Cl)([Cl:22])=O>C(Cl)Cl>[CH3:1][C:2]1([C:17]([Cl:22])=[O:19])[CH2:6][C:5]2[C:7]([CH3:16])=[C:8]([N+:13]([O-:15])=[O:14])[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 688444542,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid

生成物 1

HCID 231183052,4,6,7-Tetramethyl-5-nitro-2,3-dihydro-1-benzofuran-2-carbonyl chloride

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.5 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid, 20 ml of methylene chloride and 0.27 g of thionyl chloride were added, followed by heating at reflux for 2 hours. After returning the temperature to room temperature, the solvent was distilled off to obtain 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride. To 0.33 g of 2,3,4,9-tetrahydro-1H-beta-carboline, 0.23 g of triethylamine and 15 ml of DMF, a solution prepared by dissolving 2,4,6,7-tetramethyl-5-nitro-2,3-dihydrobenzofuran-2-carbonyl chloride in DMF was added, followed by stirring overnight at room temperature. The mixture was poured into ice-water and a crystal was collected by filtration. The crystal was dissolved in chloroform, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain 0.54 g of the objective product.

後処理

  1. temperatureby heating
  2. temperatureat reflux for 2 hours
  3. customto room temperature
  4. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-8d78fc8075284507873cff506f4e39ce
出典データセット
uspto-grants-2009_06
特許番号
US07553837B2

反応ノート

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