Pivaloyl chloride → HCID 22855818, compound

Participants

Reaction Conditions

Reaction Steps

Pivaloyl chloride (870 microliters, 1.05 equiv) was added to a solution of (2R,4S,5R,6S,8R)-2,8-dimethyl-4-hydroxy-5-benzyloxy-6-methoxy-9-t-butyldimethylsilyloxynonanol 21 (Source: Askin, D.; Volante, R. P.; Reamer, R. A.; Ryan, K. M.; Shinkai, I.; Tetra. Lett., 1988, 29, 277.) (3.07 g, 6.75 mmol) in 50 ml of anhydrous pyridine at 0° C. The solution was warmed to 25° C. over 1 hr and then was stirred at 25° C. for 16 hr. The reaction mixture was quenched by the addition of 10 ml of saturated aqueous sodium bicarbonate solution and then partitioned between75 ml of water and 150 ml of diethyl ether. The aqueous phase was extractedwith an additional 2×100 ml portions of ether. The organic phases were combined, washed with 1×50 ml of water and 1×50 ml of saturated sodium chloride solution, and dried over magnesium sulfate. Concentration in vacuo gave 3.67 g of 22 as a crude oil. The oil was purified by chromatography on 180 g of silica gel eluting with 5:1 hexanes:ethylacetate to give 3.52 g of pivaloate 22 (97% yield). The material was homogeneous by 1H and 13C NMR.

Provenance & Evidence