Sodium Hydroxide → HCID 58762516, compound

Participants

Reaction Steps

To 5-cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester (60 mg, 0.155 mmol) from Step 2 below was added NaOH (0.3 M in MeOH, 1 mL, 0.31 mmol). The solution was stirred overnight, and then quenched with 1 N HCl (5 mL). The solution was extracted with 4×10 mL CH2Cl2. The organic layer was dried over Na2SO4, and then the solids were removed by filtration. After concentrating the mother liquor, the resulting oil was purified by flash chromatography to yield the desired product (54 mg, 98% yield). 1H NMR (CDCl3) δ: 1.35-1.75 (m, 8H), 1.93-1.99 (m, 3H), 2.10 (s, 3H), 2.23 (s, 3H), 2.51 (t, J=7.33 Hz, 2H), 2.69 (d, J=16.17 Hz, 1H), 2.83 (d, J=16.18 Hz, 1H), 3.37 (s, 2H), 4.66 (s, 1H), 6.52 (s, 1H), 7.05 (s, 1H). MS (ESI): 353 (M−H).

Provenance & Evidence