Sodium hydride → HCID 22003673, compound

Participants

Reaction Steps

A stirred solution of the product from step (ix) (17.46 g) in dry N,N-dimethylformamide (300 ml) was treated with 60% dispersion of sodium hydride (3.22 g) in portions at room temperature under nitrogen. After the initial effervescence had subsided the resultant orange oil was stirred for a further 30 min before being treated with 2-(trimethylsilyl)ethoxymethyl chloride (14.3 ml) dropwise giving a pale yellow suspension which was further stirred for 30 min. The mixture was carefully poured onto water (700 ml) and extracted with ethyl acetate (3×250 ml). The combined organic extracts were further washed with water (3×250 ml) and saturated brine (250 ml) before collecting, drying over magnesium sulphate and evapoaration of the solvent under reduced pressure to give the subtitle product as a yellow oil. Yield: 26.1 g. This was not purified but used directly in the next step.

Provenance & Evidence