Sodium borohydride → HCID 57723627、化合物

温度

0 °C

To a solution of 48.4 g (199 mmol) of 4-bromo-7-fluoro-2-methylindan-1-one in 270 ml of a mixture of THF-methanol (2:1, vol.), 11.3 g (299 mmol) of NaBH4 was added in small portions, while vigorously stirring, over 2 h at 0° C. This mixture was stirred for 12 h at room temperature and then added to 500 ml of cold water. The organic layer was separated, the aqueous layer was extracted with 3×200 ml of methyl-tert-butyl ether. The combined organic extract was dried over K2CO3 and then evaporated to dryness. The residue was dissolved in 500 ml of toluene, and 2.0 g of p-TosOH was added. The resulting solution was refluxed for 4 h using a Dean-Stark trap to remove water formed and then passed through a short Silica Gel 60 column (40-63 um, d 100 mm, l 80 mm, eluent: hexanes). This column was additionally washed with 250 ml of toluene. The combined organic extract was evaporated to dryness. The residue was dried in vacuum to give the title compound. Yield 38.9 g (86%).

1. stirringThis mixture was stirred for 12 h at room temperature
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with 3×200 ml of methyl-tert-butyl ether
4. extractionThe combined organic extract
5. dry with materialwas dried over K2CO3
6. customevaporated to dryness
7. dissolutionThe residue was dissolved in 500 ml of toluene
8. addition2.0 g of p-TosOH was added
9. temperatureThe resulting solution was refluxed for 4 h
10. customto remove water
11. customformed
12. washThis column was additionally washed with 250 ml of toluene
13. extractionThe combined organic extract
14. customwas evaporated to dryness
15. customThe residue was dried in vacuum

ORDレコード

ord-4fa1f779ea6043608f2826ecb6d447fc

出典データセット

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07550544B2