Triethylamine → HCID 21968719, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-oxo-heptanoic acid 7-1 (100 g, 694 mmol), NEt3 (111.3 ml, 763.4 mmol) and THF (2000 mL) at −78° C. was added pivaloyl chloride (98.7 ml, 763.4 mmol). The mixture was warmed to 0° C. for 1.0 h and then recooled to −78° C. To a stirred solution of (S)-(−)-4-benzyl-2-oxazolidinone (136 g, 763.4 mmol) and THF (2000 ml) at −78° C. was added nBuLi (306 ml, 765 mmol, 2.5M in hexanes) dropwise over 30 minutes. After 20 minutes, the lithium reagent was transferred to the mixed anhydride via cannula. After 20 minutes, the reaction was warmed to 0° C. for 1.0 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was azeotroped with xylenes to give 7-2 as a colorless foam.

Provenance & Evidence