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

HRID 1987770노트

반응식

HRID 1987770 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8d78fc8075284507873cff506f4e39ce
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553837B2

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