8-Bromooct-1-ene → HCID 58460828, compound

Participants

Reaction Steps

Following the general procedure, 8-bromooct-1-ene (50.0 mg, 0.262 mmol) was treated with p-methoxyphenyl vinyl ether (79.0 mg, 0.5 23 mmol) and 1.2 mol % of in situ-generated complex 1a (31.0 μL, 0.10 M, 3.14 μmol; final substrate concentration=8.45 M) and allowed to stir for 16 h. The unpurified product is >98% Z (as determined by 400 MHz 1H NMR analysis). Excess p-methoxyphenyl vinyl ether was removed by vacuum distillation (1.0 torr, 80° C.). The resulting oil was purified by neutral alumina chromatography (100% hexanes to 100:1 hexanes:Et2O) to afford 10b (56.9 mg, 0.182 mmol, 69.0% yield, >98% Z isomer) as a colorless oil. IR (neat): 2924 (s), 2854 (m), 1665 (m), 1503 (s), 1463 (m), 1441 (m), 1389 (w), 1214 (s), 1180 (m), 1102 (m), 1040 (s); 1H NMR (400 MHz, CDCl3): δ 6.95-6.90 (2H, m), 6.86-6.82 (2H, m), 6.28 (1H, dt, J=6.0, 1.5 Hz), 4.73 (1H, td, J=7.4, 6.0 Hz), 3.78 (3H, s), 3.40 (2H, t, J=7.0 Hz), 2.24-2.17 (2H, m), 1.90-1.81 (2H, m), 1.49-1.32 (6H, m); 13C NMR (100 MHz, CDCl3): δ 155.2, 151.8, 141.4, 117.5, 114.8, 112.0, 55.8, 34.1, 33.0, 29.4, 28.4, 28.1, 23.9; HRMS (ESI+) [M+H]+ calcd for C15H22BrO2: 313.0803, found: 313.0800

Provenance & Evidence