反应详情

A mixture of (R/S)-ethyl 2-(6-(2,3-dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetate 52 (85 mg, 0.24 mmol) and LiOH (40 mg) in THF-H2O (1/1, 4 mL) was stirred at room temperature for 6 hours. 2N HCl was added to acidify the mixture to pH 2-3. The mixture was then extracted with EtOAc (2×20 mL). The combined organic layers were washed with water and brine, and dried over Na2SO4. The residue obtained after filtration and concentration was purified with flash chromatography (0-60% EtOAc in hexane). (R/S)-2-(6-(2,3-Dihydro-1H-inden-2-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)acetic acid (53) was obtained as colorless oil (79 mg, 96%). MS ESI (neg.) m/e: 321 (M−H). 1H NMR (500 MHz) (CDCl3) δ 7.11-7.28 (m, 5H); 6.65-6.75 (m, 2H); 5.16 (m, 1H); 3.36-3.40 (m, 3H); 3.19 (dd, J=16.6, 3.0 Hz, 2H); 2.62-2.80 (m, 3H), 2.59 (q, J=9.9 Hz, 1H), 1.99 (m, 1H), 1.78-1.87 (m, 3H).

1. extractionThe mixture was then extracted with EtOAc (2×20 mL)
2. washThe combined organic layers were washed with water and brine
3. dry with materialdried over Na2SO4
4. customThe residue obtained
5. filtrationafter filtration and concentration
6. customwas purified with flash chromatography (0-60% EtOAc in hexane)