Ammonium Chloride → 1-(4-(((4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)phenyl)prop-2-en-1-ol

Participants

Reaction Steps

To a solution of 4-(((4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)benzaldehyde (N) (15.5 mg, 0.048 mmol) in THF (1.2 mL) at 0° C. was added vinylmagnesium bromide (55 μL, 1M in THF) dropwise. After 30 minutes, saturated aqueous NH4Cl was added at 0° C., and the mixture was extracted with ether. The collected organic layers were washed with brine, dried with MgSO4, filtered and concentrated to yield the title compound (12.1 mg, 0.035 mmol, 72%). 1H NMR (CDCl3, 300 MHz) δ 7.36-7.22 (4H, m), 6.10-5.99 (1H, m), 5.34 (1H, d, J=17.1 Hz), 5.20-5.17 (2H, m), 3.88-3.81 (1H, m), 3.71-3.65 (1H, m), 2.95-2.84 (2H, m), 1.51-1.29 (12H, m), 1.37 (3H, s), 1.35 (3H, s), 0.88 (3H, t, J=4.8 Hz); LRMS (APCI+) calcd for C22H35O3 [M−H]: 345.2; found 345.4.

Provenance & Evidence