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2.3.9. Product 5i 5-Bromo-4,4-Dimethyl-6-(4-Fluorophenyl)-Tetrahydro-2H-Pyran-2-One
This protocol is extracted from research article:
δ-Lactones—A New Class of Compounds That Are Toxic to E. coli K12 and R2–R4 Strains
Materials (Basel), May 30, 2021; DOI: 10.3390/ma14112956

Colorless crystals mp. 102–103 °C; Rf = 0.23 (ethyl acetate:hexan 1:7); 1H NMR (CDCl3, 500 MHz) δ (ppm): 1.21 (s, 3H, C(CH3)2), 1.28 (s, 3H, C(CH3)2), 2.60 (d, 1H, J = 17.4 Hz, CHaHb 2.82 (d, 1H, J = 17.4 Hz, CHaHb), 4.05 (d, 1H, J = 10.8 Hz, CHBr), 5.39 (d, 1H, J = 10.8 Hz, CHAr), 7.03–7.12 (m, 2H, HAr), 7.32–7.39 (m, 2H, HAr); 13C NMR (125 MHz, CDCl3) δ (ppm): 21.3 (C(CH3)2), 29.5 (C(CH3)2), 35.3 (C(CH3)2), 44.0 (CH2), 61.3 (CHBr), 82.6 (CHAr), 168.2 (C=O), CAr: 115.5 (d, 2JF-C= 21.9 Hz), 129.4 (d, 3JF-C= 8.6 Hz), 133.1 (d, 4JF-C= 3.4 Hz), 163.0 (d, JF-C = 248.6 Hz); ESI-TOF HR: m/z calcd for C13H14BrFO2: 323.0068 [M+Na]+, found 323.0080.

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