5-hexyl-4-hydroxy-5-methylthiophen-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 33 (36 mg, 0.17 mmol) and 3-iodo-1-chlorobutane (40 μL, 0.34 mmol) following general procedure H was obtained 42 (32 mg, 75%) after flash chromatography (20% EtOAc/Hexanes). 1H NMR (400 MHz, CDCl3) δ 0.86 (t, J=5.1 Hz, 3H), 1.09-1.14 (m, 1H), 1.25 (s, 6H), 1.44-1.53 (m, 1H), 1.63 (s, 3H), 1.77-1.85 (m, 2H), 1.90-2.00 (m, 4H), 3.59 (t, J=4.5 Hz, 2H), 3.95-3.99 (m, 2H), 5.28 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 13.7, 22.3, 25.1, 26.1, 26.4, 29.1, 29.1, 31.5, 39.0, 43.9, 59.5, 71.6, 101.5, 185.9, 192.9. IR (NaCl) 2927, 1683, 1607 cm−1. Analysis Calculated for C15H25C2S: C, 59.1; H, 8.27; Found: C, 59.3; H, 8.39.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 33 (40.3 mg, 0.19 mmol) and dimethyl sulfate (35 μL, 0.37 mmol) following general procedure H was obtained 36 (25 mg, 58%) after flash chromatography (15% EtOAc/Hexanes). 1H NMR (300 MHz, CDCl3) δ 0.86 (t, J=6.7 Hz, 3H), 1.08-1.13 (m, 1H), 1.24 (s, 6H), 1.35-1.39 (m, 1H), 1.61 (s, 3H), 1.75-1.82 (m, 2H), 3.81 (s, 3H), 5.30 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 14.0, 22.5, 25.1, 26.4, 29.2, 31.5, 38.9, 59.4, 59.4, 101.3, 187.3, 193.8.