Reaction #554627

Reaction equation

5′-O-tert-butyldiphenylsilyl-2′-O—[N,N-dimethylaminooxyethyl]-5-methyluridine

Triethylamine trihydrofluoride

triethylamine

MeOH

→

2′-O-(dimethylaminooxyethyl)-5-methyluridine

Yield 92.5%

Solvents

CH2Cl2

THF

Conditions

Workup

1. 1
   OtherReaction
2. 2
   OtherSolvent was removed under vacuum
3. 3
   Washeluted with 10% MeOH in CH2Cl2

Procedure

Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5′-O-tert-butyldiphenylsilyl-2′-O—[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 2′-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%).

Source