Acetic Anhydride → HCID 12146425, compound

Participants

Reaction Steps

To a solution of (2Z,4E,6E)-2,6-difluoro-7-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid (Intermediate 22, 108 mg, 0.27 mmol) in pyridine (2 mL) at 0° C. was added acetic anhydride (100 μL, 1.1 mmol). The mixture was stirred for 4 h while warmed to ambient temperature. The reaction was quenched with aqueous Na2CO3, stirred for 30 min, acidified with 1M HCl and extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10%→50% EtOAc-hexane) to give the title compound as a yellow solid (82 mg, 69%).

Provenance & Evidence