反应 #1951031

反应方程式

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

sodium methoxide

→

4.46

收率 81.3%

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

收率 81.3%

溶剂

MeOH

反应条件

后处理

1. 1
   其他the solvent was then removed under vacuum
2. 2
   萃取the suspension extracted with EtOAc (2×50 mL)
3. 3
   干燥The combined organic extracts were dried over MgSO4
4. 4
   过滤filtered
5. 5
   其他evaporated
6. 6
   其他to yield a white solid
7. 7
   其他The solid was recrystallized

实验过程

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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