Hydrochloric Acid → HCID 14750110, compound

Temperature

-70 °C

To a solution of 12.15 g (47.6 mmol) of 4-(t-butyldimethylsiloxymethyl)heptanenitrile in 120 mL of toluene at -70° C., under argon, was added 35.3 mL (53.0 mmol) of a 1.5 M solution of diisobutylaluminum hydride in toluene. After stirring at -70° C. for 3.25 hr, 36.5 mL of methanol was added and the mixture was poured into a mixture of ca. 200 mL of ether, ca. 100 g of ice and 214 mL of 3N hydrogen chloride solution. The aquenous layer was separated and extracted with 3×200 mL of ether. The combined organic layers were washed with 120 mL of saturated sodium bicarbonate solution and 120 mL of saturated brine (a gelatinous precipitate, which resulted on washing with saturated brine, was removed by filtration through celite prior to separation of the aqueous layer), dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica gel to give 10.01 g (81.4%) of crude 4-(t-butyldimethylsiloxymethyl)heptanal; TLC (SiO2, 1:9 ethyl acetate:hexane) Rf 0.55 (PMA); IR (chloroform): μmax 1719 (aldehyde C=O) cm-1.

1. customThe aquenous layer was separated
2. extractionextracted with 3×200 mL of ether
3. washThe combined organic layers were washed with 120 mL of saturated sodium bicarbonate solution and 120 mL of saturated brine (a gelatinous precipitate, which
4. customresulted
5. washon washing with saturated brine
6. customwas removed by filtration through celite
7. customto separation of the aqueous layer),
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by column chromatography on silica gel

ORD record

ord-7ac0b076916d4a30b7ad5b90f095029e

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04897477