Hydrochloric Acid → HCID 21412035, compound

Participants

Reaction Conditions

Reaction Steps

IX (6.30 g, 0.0185 mole), hexamethyldisilazane (HMDS) (12 ml), trimethylchlorosilane (TMCS) (6 ml), and pyridine (40 ml) were mixed and kept overnight at room temperature. The resulting white suspension was evaporated to dryness (50° C, 10 mm Hg). Ether (100 ml) was added, and the suspension was filtered. The resulting clear, yellow solution of X was cooled to 0° C, and methylmagnesium bromide in ether (3.8N, 8.0 ml, 0.030 mole) was added dropwise during 20 minutes. After stirring for 2 hours at room temperature, the white suspension being formed was poured into a mixture of cold hydrochloric acid (0.25N, 140 ml) and ether (50 ml). The ethereal phase was separated, and the aqueous layer was extracted with ether (50 + 25 ml). The combined ethereal extracts were washed with water 50 ml) and dried over sodium sulfate. The solvent was removed from a water bath (60° C, 10 mm Hg), and the residual light yellowish oil (7.40 g) was distilled under reduced pressure to give 5.40 g (82%) of XI as a light yellowish oil, b0.08 203°-210° C, nD25 1.4710.

Provenance & Evidence