反应详情

温度

0 °C

To a mixture of 41.3 g (0.2 mol) of 2-(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)ethanol and 52.5 g (0.2 mol) PPh3 in 800 ml of THF 35.6 g (0.2 mol) of NBS was added at vigorous stirring for 5 min at 0° C. This mixture was stirred for 2 h at room temperature and then evaporated to dryness. A solution of the residue in 500 ml of hexanes was filtered through glass frit (G3), and the precipitate was additionally washed by 3×300 ml hexanes. The combined organic extract was evaporated to dryness. The product was isolated from the residue using flash chromatography on Silica Gel 60 (40-63 um, d 80 mm, l 250 mm; eluent: hexanes/ether=20/1, vol.). Yield 39.3 g (73%) of ca. 1 to 1 mixture of the diastereomers A and B.

1. additionwas added
2. stirringThis mixture was stirred for 2 h at room temperature
3. customevaporated to dryness
4. filtrationA solution of the residue in 500 ml of hexanes was filtered through glass frit (G3)
5. washthe precipitate was additionally washed by 3×300 ml hexanes
6. extractionThe combined organic extract
7. customwas evaporated to dryness
8. customThe product was isolated from the residue
9. additionYield 39.3 g (73%) of ca. 1 to 1 mixture of the diastereomers A and B