反応 #3190

ord-83eb8c4f8a924307bcc393ec98b1dc0e

反応方程式

CCc1c[nH]cc1CC
3,4-Diethylpyrrole
CCc1c(COC(C)=O)[nH]c(C(=O)OCc2ccccc2)c1C
benzyl 5-(acetoxymethyl)-3-methyl-4-ethyl-pyrrole-2-carboxylate
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
CCc1c(Cc2[nH]c(Cc3[nH]c(C(=O)OCc4ccccc4)c(C)c3CC)c(CC)c2CC)[nH]c(C(=O)OCc2ccccc2)c1C
powder
収率 82.0%
CCc1c(Cc2[nH]c(Cc3[nH]c(C(=O)OCc4ccccc4)c(C)c3CC)c(CC)c2CC)[nH]c(C(=O)OCc2ccccc2)c1C
2,5-Bis[[5-(benzyloxycarbonyl)-3-ethyl-4-methylpyrrol-2-yl]methyl]-3,4-diethylpyrrole
収率 82.0%

溶媒

反応条件

温度
60°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.WAITplaced in the freezer for several hours
  2. 2
    ろ過The product was then collected by filtration
  3. 3
    洗浄washed with a small amount of cold ethanol
  4. 4
    その他recrystallized from dichloromethane-ethanol

実験手順

3,4-Diethylpyrrole (2A, FIG. 2)28 (0.6, 4.9 mmol), benzyl 5-(acetoxymethyl)-3-methyl-4-ethyl-pyrrole-2-carboxylate (2B, FIG. 2)29 (2.5 g, 7.9 mmol), and p-toluenesulfonic acid (0.15 g) were dissolved in 60 mL of absolute ethanol and heated at 60° C. for 8 h under nitrogen. The resulting suspension was reduced in volume to 30 mL and placed in the freezer for several hours. The product was then collected by filtration, washed with a small amount of cold ethanol, and recrystallized from dichloromethane-ethanol to afford a white powder (2.07 g, 82%): mp 211° C. NMR spectra and high resolution mass spectral data were obtained as described and are reported 13a.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05733903uspto-grants-1998_03