Lithium Hydroxide → HCID 68879396, compound

Participants

Reaction Steps

The compound of Example 3D (360 mg, 0.408 mmol) was dissolved in 6 ml of THF and CH3OH (1:1). Then 2.5 ml of LiOH solution (1M, aqueous) was added at 0° C. The resulting mixture was stirred for 5 hour at ambient temperature. The organic solvent was removed in vacuo, and enough water was added to make one phase. The solution was acidified with acetic acid to precipitate a light yellow solid, which was extracted with EtOAc (3 times). The combined organic layer was washed with brine and dried over Na2SO4 Concentration in vacuo gave the title compound (350 mg, 98% yield). 1H NMR (300 MHz, CDCl3) δ 6.83–6.74 (m, 3 H), 5.78 (s, 1 H), 4.34 (d, J=7.2 Hz, 1 H), 3.98 (m, 1 H), 3.84 (m, 1 H), 3.52–3.33 (m, 5H), 2.92 (s, 3H), 2.80–1.10 (m, 44H), 1.89 (s, 3H), 0.99 (d, J=6.0 Hz, 3 H), 0.89 (s, 3 H), 0.69 (s, 3 H), 0.55 (s, 3 H); MS (ESI) m/e 868 (M+H)+, 866 (M−H)—.

Provenance & Evidence