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  (Nucleoside Chemistry)

Substitution (Cl)

(Aliphatic Alcohols)


Example 1

To NaH (60 wt% in mineral oil, 1.58 g, 39.6 mmol) in THF (50 mL) at RT was added the alcohol (A) (8.59 mL, 113.2 mmol) dropwise. The mixture was stirred at RT for 20 min, after which time this solution was added to the alkyl chloride (B) (9.70 g, 28.3 mmol) in THF (150 mL) at RT. The reaction mixture was stirred at RT for 1 h. The reaction mixture was poured into 50% sat aq NaHCO3. The org layer was separated and the aq layer was further extracted with ether (2x) and EtOAc (2x). The combined organics were washed with brine, dried (Na2SO4), and concentrated. The resulting crude material was purified by silica gel column chromatography (20-100% EtOAc/hexane) to provide the product. [8.16 g, 77%]

[Patent Reference: WO2014110000, page 17, (2.6 MB)]