2-Methyl-2-butene → HCID 86675860, compound

Participants

Reaction Steps

To (E)-(2R,3R,4R,5R)-3,5-Dimethoxy-2,4-dimethyl-7-tributylstannanyl-hept-6-enal (98 mg, 0.2 mmol) in tert-butanol (2 ml) and 2-methyl-2-butene (0.22 ml, 2.03 mmol) at room temperature, was added a solution of sodium chlorite (92 mg, 1.02 mmol) and sodium dihydrogenphosphate (58 mg, 0.41 mmol) in water (0.5 ml). The reaction was stirred vigorously overnight, after which brine was added and then extracted with dichloromethane (2×). The organics were dried through a hydrophobic frit and concentrated in vacuo. The oily residue was left on a vacuum pump overnight to afford the product 5b as a solid (91 mg, 90%). 1H NMR (300 MHz, CDCl3) δ 6.05 (d, J=19.0 Hz, 1H), 5.58 (dd, J=19.0 Hz, 7.9 Hz, 1H), 3.72 (m, 1H), 3.38 (s, 3H), 3.23 (t, J=8.8 Hz, 1H), 3.16 (s, 3H), 2.52 (m, 1H), 1.61 (m, 1H), 1.43 (m, 6H), 1.24 (m, 6H), 1.01 (d, J=7.0 Hz, 3H), 0.82 (m, 15H), 0.71 (d, J=7.0 Hz, 3H).

Provenance & Evidence