Tetrahydrofuran → HCID 90238651, compound

Participants

Reaction Steps

To a solution of crude (C94) (16.0 g, ≦1.112 mol) in tetrahydrofuran (600 mL) at 0° C. was added sodium hydride (60% in mineral oil, 13.5 g, 0.33 mol) portion-wise. After addition was complete, the reaction was allowed to warm to room temperature and stir at that temperature for 30 minutes. 2-Bromo-1,1-diethoxyethane (83 g, 0.33 mol) was added and the reaction was refluxed for 16 hours. The reaction mixture was cooled to room temperature and poured into ice-water (100 mL). The aqueous layer was washed with ethyl acetate (3×200 mL), and the organic phases were combined and washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (Gradient: 1% to 10% ethyl acetate in petroleum ether) provided (2S)-2-[(1R)-1-(2,2-diethoxyethoxyl)but-3-en-1-yl]tetrahydrofuran as the first eluting isomer and (2S)-2-[(1S)-1-(2,2-diethoxyethoxyl)but-3-en-1-yl]tetrahydrofuran as the second eluting isomer, both as yellow oils.

Provenance & Evidence