Lithium Hexamethyldisilazide → HCID 58962932, compound

Temperature

-40 °C

The 3-chloro-1-naphthalenecarbaldehyde (2 g) dissolved in dry THF (12 mL) was added dropwise to lithium bis(trimethylsilyl)amide 1M in THF (11.5 mL) previously cooled at −40° C. The resulting yellow mixture was stirred from −40° C. to −20° C. over 1.5 h; then it was cooled down at −50° C. and lithium aluminium hydride 1M in Et2O (10.6 mL) was added; the mixture was stirred at −40° C. for 2 h then it was quenched with HCl 2N (10 mL) and allowed to reach room temperature. The reaction mixture was diluted with further aqueous HCl 2N solution (20 mL) and extracted with CH/Et2O 1/1 (50 mL). The acidic aqueous phase was basified at 0° C. with NaOH pellets until pH=14, then it was extracted with diethyl ether (2×150 mL). The organic phase was dried and concentrated in vacuo to give the title compound (1.78 g) as a white solid.

1. temperaturethen it was cooled down at −50° C.
2. stirringthe mixture was stirred at −40° C. for 2 h
3. customit was quenched with HCl 2N (10 mL)
4. customto reach room temperature
5. additionThe reaction mixture was diluted with further aqueous HCl 2N solution (20 mL)
6. extractionextracted with CH/Et2O 1/1 (50 mL)
7. customwas basified at 0° C. with NaOH pellets until pH=14
8. extractionit was extracted with diethyl ether (2×150 mL)
9. customThe organic phase was dried
10. concentrationconcentrated in vacuo

ORD record

ord-22588ed4bb964a288d8e3670a5e529c5

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07534893B2