Allyl bromide → HCID 86749014, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 19(325 mg, 1.1 mmol) in THF (5 mL) at -78° C. was added LDA (0.5M in THF 2.4 mL) dropwise. After 15 min allyl bromide (0.16 mL, 2.2 mmol) was added and the reaction stirred at -78° C. for 1 hr followed by quenching with HOAc (0.1 mL). The reaction mixture was then diluted with ethyl acetate and then washed with water and brine, dried (MgSO4), and concentrated. Flash chromatography (silica gel, 50% ethyl acetate/hexanes) gave 20 (160 mg, 45%) as an oil. TLC Rf-0.23 (50% ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 5.80 (m, 1H), 5.10 (m, 2H), 4.10 (m, 2H), 3.32 (m, 4H), 2.70 (m, 2H), 2.56 (m, 2H), 2.20 (m, 2 H), 1.73 (m, 3H), 1.48 (s, 9H), 1.13 (m, 2H) .

Provenance & Evidence