Hexane → (4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-pentanal

Temperature

-95 °C

A 3.79 g amount of the compound (4-6), methyl(4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-heptanoate was taken in a 300 ml eggplant-shaped flask, 100 ml of hexane was added, and the solution was stirred and cooled to -95° C. Thereafter 12.3 ml of a hexane solution (0.93 mol/liter) of diisobutylaluminum hydride was added and the solution stirred for 1 hour. A 100 ml amount of methanol was used to break down the excess reducing agent, then 30 ml of a saturated aqueous solution of ammonia chloride and 50 ml of ether were added and the solution was stirred at room temperature for 1 hour. The insolubles were removed by filtration by Celite, then the solution was separated and the aqueous layer was extracted by ether. The organic layer was washed two times by saturated saline in an amount of 50 ml, then was dried over anhydrous magnesium sulfate. The desiccant was filtered out, then the solvent was distilled off under reduced pressure to obtain a crude product in an amount of 4.07 g. This was purified by a silica gel column (Merck gel: 300 g, hexane/ethyl acetate=50/1) to obtain the desired product (4-7), (4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-pentanal in an amount of 3.17 g (yield 92%).

1. stirringthe solution stirred for 1 hour
2. stirringthe solution was stirred at room temperature for 1 hour
3. customThe insolubles were removed by filtration by Celite
4. customthe solution was separated
5. extractionthe aqueous layer was extracted by ether
6. washThe organic layer was washed two times by saturated saline in an amount of 50 ml
7. dry with materialwas dried over anhydrous magnesium sulfate
8. filtrationThe desiccant was filtered out
9. distillationthe solvent was distilled off under reduced pressure
10. customto obtain a crude product in an amount of 4.07 g
11. customThis was purified by a silica gel column (Merck gel: 300 g, hexane/ethyl acetate=50/1)

ORD record

ord-6b646d3458004bd5bbed5c1ccebb1831

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719297