Acetic Acid → HCID 18394787, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 13-3 (2.2 g, 11.6 mmol) in THF (45 mL) at -78° C. was added a solution of LDA (6.39 mL, 12.8 mmol; 2M/THF, ethylbenzene). The mixture was warmed to -15° C. for 20 minutes, then recooled to -78° C., and 2,4,6-triisopropylbenzenesulfonyl azide (4.31 g, 13.9 mmol, prepared as described in Harmon, et al, J. Org. Chem. 1973, 38, 11-16. ) was added rapidly as a solution in 40 mL THF at -78° C. After 10 minutes, glacial acetic acid (2.67 mL, 47 mmol) was added, and the resultant viscous liquid mixture allowed to warm to ambient temperature and stir for 1 hour. The solvent was then evaporated, the residue dissolved in CHCl3, washed with NaHCO3 (sat.), and dried over magnesium sulfate. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 25% ethyl acetate/hexanes) to give 13-4 as a colorless oil.

Provenance & Evidence