1-(2-Furyl)heptanol (1c) – Oil. 1H-NMR (CDCl3) δ: 7.38 (m, 1 H), 6.33 (m, 1 H), 6.20 (m, 1 H), 4.64 (t,
1 H, J = 7 Hz), 2.05 (br s, 1 H), 1.80 (m, 2 H), 1.23 (m, 8 H), and 0.86 ppm (t, 3 H, J = 7 Hz).
5-Methyl-2-furylbenzyl alcohol (6a) – Oil. 1H-NMR (CCl4) δ: 7.22 (m, 5 H), 5.76 (m, 2 H), 5.50 (s, 1 H),
3.30 (br s, 1 H), 2.18 (s, 3 H). IR (film) νmax: 3600, 3012, 1584, and 1560 cm-1.
5-Methyl-2-furyl-2-thienylmethanol (6b) – Oil. 1H-NMR (CCl4) δ: 7.05 (m, 1 H), 6.75 (m, 2 H), 5.93 (m,
1 H), 5.72 (m, 2 H), 2.98 (br s, 1 H), 2.22 (s, 3 H). IR (film) νmax: 3390 and 1560 cm-1.
Thermal isomerization of 2-furylcarbinols in water – General procedure.
2-Furylcarbinol (100 mg) was suspended in redistilled water (50 mL) and the mixture was stirred at reflux
temperature (Table 1). After the reaction was completed the reaction mixture was extracted many times
with ether and the extracts were then dried (Na2SO4). Evaporation of the solvent yielded a crude product
which was chromatographed on silica gel eluting with 4:1 n-hexane/ethyl acetate.
2-Phenyl-4-hydroxycyclopent-2-en-1-one (3a). mp 58-59 °C (lit.,5 58-59 °C). Calcd for C11H10O2: C
1
75.84, H 5.79; Found C 75.90, H 5.71. H-NMR (CDCl3) δ: 7.67 (m, 2 H), 7.65 (m, 1 H), 7.38 (m, 3 H),
5.01 (m, 1 H), 2.96 (dd, 1 H, J1 = 18.5 Hz, J2 = 6.1 Hz), 2.8 (br s, 1 H), and 2.48 ppm (dd, 1 H, J1 = 18.5
Hz, J2 = 2 Hz). MS, m/z: 175 (7%), 174 (55), 146 (23), 145 (26), 131 (18), 129 (14), 128 (19), 127 (14),
117 (18), 115 (16), 105 (12), 104 (100), 103 (25), 102 (34), 78 (10), 77 (22), 76 (12).
2-(2-Thienyl)-4-hydroxycyclopent-2-en-1-one (3b) – Oil. Calcd. for C9H8O2S: C 59.98, H 4.47, S 17.79;
Found C 60.1, H 4.4, S 17.9. 1H-NMR (CDCl3) δ: 7.46 (m, 1 H), 6.94 (m, 1 H), 6.70 (m, 2 H), 4.87 (m, 1
H), 3.6 (br s, 1 H), 2.28 (dd, 1 H, J1 = 18.5 Hz, J2 = 6.1 Hz), and 2.32 ppm (dd, 1H, J1 = 18.5 Hz, J2 = 2
Hz). MS, m/z: 181 (16%), 180 (100), 179 (12), 152 (35), 151 (53), 137 (28), 136 (12), 135 (47), 134 (15),
124 (13), 123 (23), 111 (21), 110 (47), 109 (27), 108 (37), 97 (21), 91 (33), 84 (17), 82 (14), 69 (30), 65
(20), 63 (18).
5-n-Hexyl-4-hydroxycyclopent-2-en-1-one (2c) – Oil. Calcd for C11H18O2: C 72.49, H 9.95; Found C
72.40, H 10.03. 1H-NMR (CDCl3) δ: 7.50 (dd, 1H, J1 = 5.7 Hz, J2= 2.3 Hz), 6.16 (dd, 1 H, J1 = 5.7 Hz, J2
= 1.3 Hz), 4.66 (m, 1 H), 3.0 (br s, 1H), 2.20 (m, 1 H), 1.80 (m, 2 H), 1.27 (m, 8 H), and 0.86 ppm (t, 3 H,
J = 6.8 Hz). MS, m/z: 182 (10%), 153 (18), 139 (20), 138 (100%), 135 (13), 121 (10), 113 (20), 112 (14),
111 (30), 109 (20), 107 (10), 97 (18), 96 (20), 95 (24), 93 (10), 83 (16), 81 (12), 79 (12), 69 (26), 67 (18).