Sodium hydride → HCID 131735515, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 14B (15.1 g, 41.0 mmol) in tetrahydrofuran under nitrogen was cooled to −8° C. and 60% sodium hydride in mineral oil (2.461 g, 61.5 mmol) was added in portions at a rate such that the temperature was maintained at or below −5° C. The solution was stirred 30 minutes at −5° C. and 2-(trimethylsilyl)ethoxymethyl chloride (8.73 mL, 49.2 mmol) was added dropwise over 15 minutes. The mixture was stirred for 30 minutes at −5° C. and allowed to warm to ambient temperature and stirred overnight. The reaction was quenched carefully with aqueous saturated ammonium chloride and diluted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified on an Analogix MPLC using a silica gel column eluting with 100% heptane followed by 7% ethyl acetate/heptanes to provide the title compound. MS (ESI+) m/z 498.8 (M+H)+.

Provenance & Evidence