J. Org. Chem. 1983,48, 1552-1554
1552
IR [(neat) 1720 cm-'L NMR [(CDCl,) 6 2.35 (t, 4 H, J = 7.5 Hz)], and MS [m/z 156 (M+)] are in accord with literature values reported for 5.12 GC analysis of the crude reaction mixture revealed the presence of ca. 10% of the di-n-butylcarbinol(158 "C, column 1): IR (neat) 3500 cm-*;MS, m / z 196 (M - HzO), 157 (M- CIHB,base peak), 143 (M - C5Hll). Quenching Experiment for the Reaction of Acid la with Methyllithium. A solution of 0.200 g (1.4 mmol) of la in 20 mL of dry THF was cooled to 0 "C (ice bath) and was treated, with
stirring, with 9.0 mmol of methyllithium. With the addition complete (
