تفاعل #1951034

معادلة التفاعل

2,5,6-Trichloro-3-(2-furyl)-1-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)indole

sodium methoxide

MeOH CHCl3

→

4.78

المردود 75.6%

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

المردود 75.6%

المذيبات

MeOH

CHCl3

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONwere completely dissolved
2. 2
   أخرىThe solvent was then removed under vacuum
3. 3
   استخلاصThe aqueous suspension was extracted with EtOAc (2×50 mL)
4. 4
   تجفيفthe combined organic extracts were dried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىto yield a clear oil
8. 8
   workup.ADDITIONFractions containing product
9. 9
   أخرىevaporated
10. 10
    أخرىto yield a pale yellow solid which
11. 11
    أخرىwas recrystallized from 10% MeOH/CHCl3 and hexane

الإجراء التجريبي

2,5,6-Trichloro-3-(2-furyl)-1-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)indole (4.76, 142 mg, 0.22 mmol) was suspended in dry MeOH (10 mL) to which was added sodium methoxide (30 mg, 0.56 mmol). The suspension was stirred at room temperature for 45 min, until the solids were completely dissolved. The solvent was then removed under vacuum, and the residue suspended in brine (50 mL). The aqueous suspension was extracted with EtOAc (2×50 mL), and the combined organic extracts were dried over MgSO4, filtered and evaporated to yield a clear oil. The oil was dissolved in CHCl3 (1 mL) and subjected to column chromatography (40×350 mm) on silica gel with 10% MeOH/CHCl3. Fractions containing product were pooled and evaporated to yield a pale yellow solid which was recrystallized from 10% MeOH/CHCl3 and hexane to yield 67 mg (75%) of 4.78 as a white crystalline solid: mp 140-141 C; Rf0.5 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.46 (s, 1H), 8.14 (s, 1H), 7.86 (s, 1H), 6.88 (d, 1H), 6.68 (s, 1H), 6.47 (dd, 1H), 5.42 (d, 1H, D2O exch.), 5.23 (s, 1H, D2O exch.), 4.45 (d, 1H), 3.89 (d, 1H), 3.73 (s, 2H), 2.55 (m, 1H), 2.13 (m, 1H). 13C-NMR (125 MHz, DMSO-d6): δ 146.54, 142.25, 132.30, 125.61, 124.39, 124.09, 122.64, 120.75, 114.98, 111.51, 106.91, 104.87, 87.25, 85.04, 69.98, 60.91, 38.97. HRMS (EI) m/z calcd. for C17H14Cl3NO4 400.9988, found 400.9986. Anal calcd for C17H14Cl3NO4.¼H2O: C, 50.15; H, 3.59; N, 3.44. Found: C, 50.17; H, 3.65; N, 3.43.

المصدر