Ution was refluxed with stirring for 1 h in an oil bath at 85 C. After cooling the reaction solution to room temperature, 1 N HCl (70 mL) was added. The resulting precipitate was filtered and washed with cold water and dried to offer crude 78 (0.1041 g, 82). The crude 78 was dissolved in hot ethyl acetate (5.0 mL), and theInt. J. Mol. Sci. 2021, 22,33 ofhomogenous option was concentrated, filtered, and washed with hexanes to give pure 78 (0.0734 g, 58) as a white strong (251.554.six C): 1 H NMR (400 MHz, CDCl3) 9.13 (s, 2H), 7.30 (d, J = 1.6, 1H), 7.29 (d, J = 8.4, 1H), 7.15 (dd, J = eight.0, two.0, 1H), 1.81 (m, 2H), 1.68 (s, 4H), 1.53 (m, 2H), 1.28 (s, 6H), 1.26 (s, 6H); 13 C NMR (one hundred.six MHz, CDCl3) 177.six, 167.7, 158.eight, 158.3, 144.7, 143.four, 137.6, 128.9, 127.eight, 126.4, 119.four, 35.1, 35.0, 34.two, 34.0, 33.two, 31.9, 31.eight, 20.9, 20.9; IR (neat) 2957, 1679.64 cm- 1 . ES-MS (M Na) calcd for C22 H26 N2 O2 Na 373.1892, found 373.1898. six.51. Methyl 2-fluoro-4-(1-(5,five,eight,8-tetramethyl-5,six,7,8-tetrahydronaphthalen-2-yl) vinyl)benzoate (79) To a 250 mL flask, ketone product 75 (0.7971 g, two.16 mmol) was combined with dry THF (four.0 mL) at area temperature along with a triphenylphosphonium methylide solution– created in the addition of methyltriphenylphosphonium bromide (1.15 g, three.22 mmol) to a answer of n-butyl lithium (two.7 mL, 1.6 M in hexanes, four.32 mmol) and diisopropyl amine (66 mL, four.67 mmol) in THF (2 mL)–was added with stirring. The reaction was stirred for thirty minutes, poured into water, and MTIC-d3 Epigenetic Reader Domain extracted with ethyl acetate. The organic extracts have been washed with water, dried more than sodium sulfate, and purified by column chromatography (150 mL SiO2) with two.5 ethyl acetate/hexanes to five ethyl acetate/hexane S 24795 Autophagy providing pure compound 79 (0.4454 g, 56) as yellow strong, mp 80.86.5 C: 1 H NMR (400 MHz, CDCl3) 7.90 (t, J = 7.6, 2H), 7.28 (d, J = 8.0, 1H), 7.22 (dd, J = eight.0, 1.6, 1H), 7.21 (dd, J = 2.0, 1H), 7.14 (dd, J = 12.4, 1.two, 1H), 7.05 (dd, J = eight.four, 2.0, 1H), 5.54 (d, J = 0.eight, 1H), five.50 (d, J = 0.eight, 1H), 1.69 (s, 4H), 1.30 (s, 6H), 1.24 (s, 6H); 13 C NMR (100.six MHz, CDCl3) 164.eight, 164.7, 163.0, 160.4, 148.five, 148.four, 148.3, 148.two, 145.0, 144.8, 136.9, 131.8, 126.5, 126.2, 125.three, 123.7, 123.7, 117.three, 117.two, 116.7, 116.4, 115.7, 52.two, 35.0, 34.9, 34.two, 34.1, 31.7. ES-MS (M Na) calcd for C24 H27 FO2 Na 389.1893, found 389.1892. 6.52. 2-fluoro-4-(1-(5,five,8,8-tetramethyl-5,six,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic Acid (36) Compound 36 was synthesized in line with the technique of Boehm and co-workers. Compound 79 (two.0486 g, 5.59 mmols) and methanol (36.0 mL) had been added to a option of potassium hydroxide (0.9348 g, 16.66 mmols) in water (1.34 mL). The reaction was refluxed, and after 70 min of reflux, the answer was cooled to space temperature plus the crude product was precipitated with 1 N hydrochloric acid (560 mL) to offer crude item (1.7523 g) 36. It was then purified by column chromatography (150 mL SiO2) in 50 ethyl acetate/hexane to give pure 36 (1.5974 g, 81.0) as white crystalline strong, mp 165.683.0 C: 1 H NMR (400 MHz, CDCl3) eight.01 (t, J = 8.0, 2H), 7.29 (d, J = eight.4, 1H), 7.27 (dd, J = eight.four, 1.6, 1H), 7.23 (d, J = two.0, 1H), 7.18 (dd, J = 12.0, 1.2, 1H), 7.06 (dd, J = 8.4, 2.0, 1H), five.58 (d, J = 0.4, 1H), five.54 (d, J = 0.4, 1H), 1.70 (s, 4H), 1.31 (s, 6H), 1.26 (s, 6H); 13C NMR (100.six MHz, CDCl3) 169.five, 169.4, 163.eight, 161.2, 149.7, 149.six, 148.2, 148.two, 145.1, 144.9, 136.eight, 132.four, 126.5, 126.three, 125.three, 123.9, 123.eight, 116.eight, 116.6, 116.3, 116.2, 116.1, 35.0, 34.9, 34.
