Reaktion #1951031

Reaktionsgleichung

2,5,6-Trichloro-3-acetyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole

sodium methoxide

→

4.46

Ausbeute 81.3%

2,5,6-Trichloro-3-acetyl-1-(β-D-ribofuranosyl)indole

Ausbeute 81.3%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was then removed under vacuum
2. 2
   Extraktionthe suspension extracted with EtOAc (2×50 mL)
3. 3
   TrocknenThe combined organic extracts were dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto yield a white solid
7. 7
   SonstigeThe solid was recrystallized

Vorschrift

2,5,6-Trichloro-3-acetyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole (4.43, 232 mg, 0.53 mmol) was dissolved in dry MeOH (20 mL) to which was added sodium methoxide (35 mg, 0.65 mmol). The solution was stirred at room temperature for 45 min, and the solvent was then removed under vacuum. The residue was suspended in 10% aqueous NaHCO3 (50 mL) and the suspension extracted with EtOAc (2×50 mL). The combined organic extracts were dried over MgSO4, filtered and evaporated to yield a white solid. The solid was recrystallized from boiling EtOAc/hexane to yield 170 mg (81%) of 4.46 as a white crystalline solid: mp 249-250 C; Rf0.4 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.63 (s, 1H), 8.41 (s, 1H), 6.07 (d, 1H), 5.45-5.42 (m, 2H, D2O exch.), 5.30 (d, 1H, D2O exch.), 4.44 (q, 1H), 4.17 (d, 1H), 4.03 (d, 1H), 3.75 (b, 2H), 2.63 (s, 3H). 13C-NMR (125 MHz, DMSO-d6): δ 192.17, 133.10, 132.38, 126.21, 126.00, 125.73, 122.00, 115.44, 112.99, 88.97, 86.39, 71.63, 69.54, 60.97, 30.72. HRMS (ES) m/z calcd. for C15H14C13NO5□Na 415.9835, found 415.9843. Anal calcd for C15H14Cl3NO5: C, 45.65; H, 3.58; N, 3.55. Found: C, 45.75; H, 3.78; N, 3.61.

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