Hexamethyldisilazane → HCID 22882484, compound

Temperature

30 °C

255 ml of a 1.6M butyllithium solution in hexane are added to a solution of 85 ml of hexamethyldisilazane in 800 ml of tetrahydrofuran at -40° C. After 15 min, 140 g of methyltriphenylphosphonium bromide are added at 0° C. and the reaction mixture is stirred at 30° C. for 30 min. 77 g of 3-tert-butoxycarbonyl-2,2-dimethyl-4(S)-(2-formyl-2-methylpropyl)-1,3-oxazolidine, dissolved in 200 ml of tetrahydrofuran, are then added to the reaction solution at -30° C. The reaction mixture is stirred at room temperature for 1 h, and 600 ml of hexane are then added at 0° C. The triphenylphosphinoxide which has precipitated out is filtered off and, after dilution with 400 ml of saturated ammonium chloride solution, the filtrate is extracted with diethyl ether. The crude product is purified by means of FC (400 g of silica gel, mobile phase G): Rf (D)=0.55, Rf (ethyl acetate)=0.44; [α]D =+4.2 (c=1.25 in CHCl3); MS: (M)+ =283.

1. additionare then added to the reaction solution at -30° C
2. stirringThe reaction mixture is stirred at room temperature for 1 h
3. customThe triphenylphosphinoxide which has precipitated out
4. filtrationis filtered off
5. extractionafter dilution with 400 ml of saturated ammonium chloride solution, the filtrate is extracted with diethyl ether
6. customThe crude product is purified by means of FC (400 g of silica gel, mobile phase G)

ORD record

ord-f181a1f8064a4a86a0089d31b5e9c03e

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719141