3-Methylbenzeneethanol → HCID 58661649, 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-(3-methylphenyl)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 predominant component was the product by HPLC (partially deprotected products were also seen). The reaction was then cooled to room temperature, carefully quenched with water (40 mL), and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (120 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to afford a brown oil. This material was purified by passing through a plug of silica gel, eluting with CH2Cl2, 5% methanol in CH2Cl2, and 10% methanol in CH2Cl2. Those fractions containing products were combined and evaporated to dryness, to afford a mixture of starting material and monosilyl-protected and disilyl-protected alkylated products in a ratio of 2:5:12. This mixture was used without further purification in the next step.

Provenance & Evidence