Trimethylsilylacetylene → HCID 20778052, compound

Participants

Reaction Steps

2 g of 2′-deoxy-5-iodo-5′-O-(4-methoxytrityl)-uridine (3.19 mmole) prepared in 1-1) together with (PPh3)2PdCl2 (0.1 eq) and 61 mg of CuI (0.1 eq), were dried under a vacuum, TEA and THF in a ratio of 3:1 were added thereto, and the mixture was purged several times with argon. 0.59 ml of TMS-acetylene (1.3 eq) was then added to the mixture at a temperature ranging from 45 to 50° C., until it became black. The resulting mixture was heated for additional 3 hours to terminate the reaction, and subjected to column chromatography (silica gel 60, 230˜400 meshes, Merck) to obtain the title compound as a pale yellow solid. The chromatography was conducted using a mixture of hexane and ethyl acetate as an elution solution whose mix ratio was gradually varied from 3:1 to 1:1 (v/v).

Provenance & Evidence