Dimethylformamide → HCID 86747527, compound

Participants

Reaction Steps

To a stirred solution of 13 (1.5 g, 17 mmol) in DMF (75 mL) at ambient temperature was added LiN(TMS)2 (1M in hexanes, 17 mL) to effect a precipitate. Allyl bromide (1.6 mL, 19 mmol) was then added to the reaction mixture. After 15 min the homogeneous mixture was treated again with LiN(TMS)2 (14 mL) followed by the iodide 10 (5.9 g, 17 mmol) after 5 min. The reaction was stirred for 20 hr then diluted with ether. The ether portion was washed with water (2×), 5% KHSO4 and brine, dried (Mg SO4), and concentrated. Flash chromatography (40% ethyl acetate/hexanes) gave 14 (0.8 g, 15%) as a colorless oil.

Provenance & Evidence