反应详情

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).

1. customquenched with 1 N HCl (5 mL)
2. extractionThe solution was extracted with 4×10 mL CH2Cl2
3. dry with materialThe organic layer was dried over Na2SO4
4. customthe solids were removed by filtration
5. concentrationAfter concentrating the mother liquor
6. customthe resulting oil was purified by flash chromatography