反应详情

A solution of (1RS, 2SR, 3RS)-3-[2-(methoxymethoxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (0.2 g, 0.39 mmol) in dichloromethane (4 ml) and pyridine (28 μl, 1.6 mmol) was cooled to 0° C. under argon. To this solution was added thionyl chloride (60 μl, 0.8 mmol). The mixture was allowed to warm to ambient temperature over 20 min. and the volatiles removed in vacuo. The residue was redissolved in toluene and evaporated in vacuo (twice). The residue was dissolved in dichloromethane (4 ml) and triethylamine (250 μl) added. To this solution at room temperature under argon was added 2-mercaptopyridine-N-oxide (120 mg, 0.8 mmol) dissolved in dichloromethane (1 ml). After stirring for 20 min at room temperature t-butylthiol (450 μl, 4 mmol) was added and the mixture irradiated for 20 min (150 watt spotlight). The volatiles were removed in vacuo and the product partitioned between ethyl acetate and 3M-aq. HCl. The organic extract was washed with water, sat. aq. NaHCO3 solution and finally brine. After drying (MgSO4 anhydrous), the product was filtered and evaporated. Purification by column chromatography gave the title compound (0.075 g, 41%).

1. customthe volatiles removed in vacuo
2. dissolutionThe residue was redissolved in toluene
3. customevaporated in vacuo (twice)
4. dissolutionThe residue was dissolved in dichloromethane (4 ml)
5. additiontriethylamine (250 μl) added
6. additionwas added
7. customthe mixture irradiated for 20 min (150 watt spotlight)
8. customThe volatiles were removed in vacuo
9. customthe product partitioned between ethyl acetate and 3M-aq
10. extractionThe organic extract
11. washwas washed with water, sat. aq. NaHCO3 solution and finally brine
12. dry with materialAfter drying (MgSO4 anhydrous)
13. filtrationthe product was filtered
14. customevaporated
15. customPurification by column chromatography