Reaktion #6757

ord-7b901fc15a6e4f8abc6c1204b5292bcc

Reaktionsgleichung

CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1
4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole
CC(=O)O
acetic acid
CC(=O)OC(C)=O
acetic anhydride
→
CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1
1-acetyl-4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methylpyrazole

Edukte

CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1
4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole
CC(=O)O
acetic acid
CC(=O)OC(C)=O
acetic anhydride

Reagenzien

Keine

Lösungsmittel

C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe reaction mixture was concentrated under reduced pressure, and diethyl ether
  2. 2
    workup.ADDITIONwas added to the residue
  3. 3
    SonstigeThe resulting precipitated crystal
  4. 4
    Filtrationwas collected by filtration

Vorschrift

To a solution of 4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole (0.41 g) in tetrahydrofuran (10 mL) were added acetic acid (0.11 mL) and acetic anhydride (0.18 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and diethyl ether was added to the residue. The resulting precipitated crystal was collected by filtration to give 1-acetyl-4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methylpyrazole (0.36 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084123B2uspto-grants-2006_08