2-Cyclohexylethanol → HCID 58661652, compound

Participants

Reaction Conditions

Reaction Steps

To a dry 250-mL, 3-neck roundbottom flask was added 2-chloro-2′,3′,5′-tri-O-(TERT-butyldimethylsilyl)adenosine (5 g, 7.8 mmol, Example 1) and 2-(cyclohexyl)ethanol (15 mL). The mixture was flushed with nitrogen for 5–10 minutes, then heated to 50° C. To this mixture was added sodium hydride (1.56 g, 39 mmol, as a 60% dispersion in mineral oil) at such a rate as to avoid excessive gas evolution. The reaction was maintained at 50° C. until the reaction was complete by HPLC. The reaction was then cooled to room temperature, carefully quenched with water (50 mL), and extracted with ethyl acetate (100 mL, 2×60 mL). The combined organic extracts were washed with brine (100 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to afford a viscous oil. This material was purified by passing through a plug of silica gel, eluting with CH2Cl2, 2% MeOH in CH2Cl2, 5% MeOH in CH2Cl2, and 10% MeOH in CH2Cl2. Those fractions containing products were combined and evaporated to dryness, to afford a mixture of monosilyl-protected and disilyl-protected alkylated products (LC/MS m/z=622 and 508). This mixture was used without further purification in the next step.

Provenance & Evidence