Allyl bromide → HCID 10489752, compound

Participants

Reaction Steps

In a dry apparatus a solution of 12 (2.05 g, 7.60 mmol) in THF (15 mL) was added dropwise to magnesium powder (0.22 g, 9.1 mmol) under argon. After the addition was completed the mixture was refluxed for 45 min. Then the mixture was cooled to rt and allyl bromide (720 μL, 8.30 mmol) dissolved in THF (10 mL) was added slowly. The mixture was stirred for 4.5 h, then quenched with satd aq NH4Cl (25 mL) and extracted with ether. The combined organic phases were washed with aq NaHCO3 (5%) and brine and dried (Na2SO4). The solvents were removed under reduced pressure and the residue was crystallized from hexanes and filtered. The filtrate was purified by column chromatography (silica, ether/hexanes, 1:4), affording a light yellow oil (1.04 g, 59%). IR (neat): {tilde over (v)} 3077, 2955, 2904, 2846, 1639, 1619, 1517; 1H NMR δ 0.79 (s, 3H), 1.29 (s, 3H), 3.38 (d, 3J=6.6 Hz, 2H), 3.64 (d, 2J=11.0 Hz, 2H), 3.76 (d, 2J=11.0 Hz, 2H), 5.00-5.10 (m, 2H), 5.37 (s, 1H), 5.86-6.01 (m, 1H), 7.19, 7.43 (AA′BB′, 2×2H); 13C NMR (APT) δ 21.7 (−), 22.9 (−), 30.0 (+), 39.8 (+), 77.5 (+), 101.5 (−), 115.6 (+), 126.1 (−), 128.4 (−), 136.3 (+), 137.2 (−), 140.5 (+); GC-MS (EI) obsd 232, 231, 191, 163, 145, 115, 105, 91, 69, 56, 41; Anal. Calcd for C15H20O2: C, 77.55; H, 8.68. Found: C, 77.52; H, 8.77.

Provenance & Evidence