Sodium Hydroxide → HCID 89627666, compound

Participants

Reaction Conditions

Reaction Steps

To 1-[11-(2-ethylhexyl)-5-(4-fluoro-benzoyl)-11H-benzo[a]carbazol-8-yl]-3,5,5-trimethyl-hexan-1-one (1.18 g; 2.00 mmol) in pyridine (5 mL) are added 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol (0.24 g; 0.90 mmol) and sodium hydroxide (0.16 g; 4 mmol) at 80° C., and the mixture is stirred at 100° C. for 43 hours. After the reaction is completed, the reaction mixture is cooled to room temperature, and poured into ice water. The crude product is extracted with ethyl acetate, and the combined organic layer is washed with water and brine, dried over MgSO4, and concentrated to give a yellow resin. The crude is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1) to give a yellow solid (0.40 g; 32%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.81-0.92 (m), 1.03 (d), 1.18-1.46 (m), 2.27-2.35 (m), 2.89-2.96 (m), 3.02-3.08 (m), 4.60 (t), 4.74 (m), 7.06 (d), 7.58 (m), 7.66 (t), 7.99 (m), 8.14 (dd), 8.33 (s), 8.43 (d), 8.61 (d), 8.68 (d); 19F-NMR spectrum (CDCl3). δ [ppm]: −123.32, −119.45.

Provenance & Evidence