Helvetica Chimica Acta – Vol. 98 (2015)
799
Synthesis of 5-Hexyl-4-methyl-g-butyrolactone (¼ 5-Hexyldihydro-4-methylfuran-2(3H)-one; 1 (cis/
trans mixture)). To a stirred soln. of 4 (3.0 g, 0.014 mol) in MeOH at 08 was added NaBH4 (1.06 g,
0.028 mol). After stirring for 2 h, the mixture was slowly warmed to r.t. The mixture was poured into ice-
water, extracted with AcOEt (3 Â 20 ml), dried (MgSO4), filtered, concentrated, and the residue purified
by flash chromatography (PE/AcOEt 5 :1) to give the product as a colorless liquid (2.06 g, 80%, dr 1:1).
IR (neat): 2931, 2858, 1781, 1458, 1210, 1166, 1078. 1H-NMR (CDCl3): 4.41 – 4.36 (m, 0.5 H); 3.98 – 3.93
(m, 0.5 H); 2.67 – 2.50 (m, 1.5 H); 2.21 – 2.10 (m, 1.5 H); 1.65 – 1.53 (m, 1.5 H); 1.47 – 1.45 (m, 1.5 H);
1.30 – 1.24 (m, 7 H); 1.09 (d, J ¼ 6.4, 1.5 H); 0.96 (d, J ¼ 6.4, 1.5 H); 0.84 (t, J ¼ 6.4, 3 H). 13C-NMR
(CDCl3): 177.0; 176.6; 87.5; 83.7; 37.6; 37.2; 36.1; 34.1; 33.1; 31.7; 30.0; 29.2; 29.1; 25.9; 25.8; 22.6; 17.5;
14.1; 13.9. HR-EI-MS: 184.1459 (C11H20Oþ2 ; calc. 184.1463)
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Received October 11, 2014