Chlorotrimethylsilane → AGN-PC-009ZHB

A solution of 1.6M n-butyllithium/n-hexane solution (100 ml) was dropwise added to a solution of diisopropylamine (22.4 ml) in dry tetrahydrofuran (50 ml) at -10° C., and the mixture was stirred for 1 hour. A solution of 3-hydroxy-3-methyl-2-butanone (8 ml) in dry tetrahydrofuran (50 ml) was dropwise added at -10° C. and the mixture was stirred for 1 hour. Then, trimethylchlorosilane (20.4 ml) was dropwise added at -10° C. After stirring at 4° C overnight, the reaction mixture was filtered with celite and the solid was washed with diethyl ether (500 ml). The combined filtrate was washed with 1N hydrochloric acid (150 ml×2) and a saturated aqueous solution of NaHCO3 (150 ml×2), and dried over MgSO4. The solvent was distilled away under reduced pressure. The residue was distilled under reduced pressure to give 16 g of the title compound (bp=85°-90° C./20 mmHg) as colorless liquid (see Table 2).

1. stirringthe mixture was stirred for 1 hour
2. stirringAfter stirring at 4° C overnight
3. filtrationthe reaction mixture was filtered with celite
4. washthe solid was washed with diethyl ether (500 ml)
5. washThe combined filtrate was washed with 1N hydrochloric acid (150 ml×2)
6. dry with materiala saturated aqueous solution of NaHCO3 (150 ml×2), and dried over MgSO4
7. distillationThe solvent was distilled away under reduced pressure
8. distillationThe residue was distilled under reduced pressure

ORD record

ord-9d169289d2124786b7dd916a0136e255

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05750696