Sodium Chloride → HCID 67460237, compound

Participants

Reaction Steps

In a nitrogen stream, dioxane-water (10:1)(12 mL) was added to a mixture of trifluoromethanesulfonic acid (3R,4R,5S,6R)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)cyclohex-1-enyl ester (656 mg, 0.981 mmol), K3PO3 (250 mg, 1.18 mmol), KBr (140 mg, 1.18 mmol), 3-(4-ethylbenzyl)phenylboronic acid (283 mg, 1.18 mmol) and Pd(PPh3)4 (56.6 mg, 0.049 mmol), and the reaction mixture was heated and stirred at a temperature of 100° C. to 105° C. for 26 hours. After cooling the reaction mixture, a saturated sodium chloride aqueous solution and water were added thereto. The resulting solution was extracted with ether, and the organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10 to 1:8) to obtain the title compound (510.0 mg, 73%).

Provenance & Evidence