Propanal → HCID 131731945, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4S,5S)-4-heptyl-2,2-dimethyl-5-(prop-2-ynyl)-1,3-dioxolane (19.4 mg, 0.081 mmol) in THF (0.8 mL) at −78° C. was added n-butyllithium (51 μL, 1.6 M). The mixture was stirred for 30 min. at which time propanal (excess) was added. The mixture was stirred at −78° C. for an additional 30 min. The reaction was quenched with sat'd NH4Cl (aq.) at −78° C. The title compound was isolated using a standard workup (22 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 4.30 (m, 1H), 3.81 (dt, 4 Hz, 7.6 Hz, 1H), 3.71 (m, 1H), 2.54 (dd, 1.6 Hz, 5.2 Hz, 2H), 1.39 (s, 6H), 1.28 (m, 12H), 0.99 (t, 7.6 Hz, 3H), 0.87 (t, 6.4 Hz, 3H). LRMS (APCI+) found 279.7, [M−H2O]+.

Provenance & Evidence