HCID 86624017, compound → HCID 66750500, compound

Participants

Reaction Conditions

Reaction Steps

MeLi (32 mL, 51 mmol, 1.6 M in diethyl ether) is added to a suspension of methyltriphenylphosphonium bromide (27.8 g, 77.8 mmol) in THF (100 mL) at 0° C. The mixture is stirred at 0° C. for 30 min. Then a solution of (R)-2-(4-Methoxy-2-vinylbenzyl)-butyraldehyde (6.12 g) in THF (50 mL) is added. The mixture is stirred at 0° C. for 1 h. The mixture is partitioned between EtOAc and aq. NH4Cl. The organic extract is dried with MgSO4, concentrated and purified to give the title compound as an oil: 1H NMR (CDCl3) δ 0.85 (t, J=7.3 Hz, 3H), 1.23-1.28 (m, 1H), 1.42-1.47 (m, 1H), 2.09-2.14 (m, 1H), 2.56-2.69 (m, 2H), 3.81 (s, 3H), 4.85 (d, J=17 Hz, 1H), 4.93 (dd, J=2, 10 Hz, 1H), 5.27 (dd, J=1, 11 Hz, 1H), 5.50-5.65 (m, 2H), 6.74 (dd, J=3, 8 Hz, 1H), 6.94 (dd, J=11, 17 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 7.02 (d, J=3 Hz, 1H).

Provenance & Evidence