C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF NATURALLY OCCURRING SUBSTANCES .64. STRUCTURE OF MORONIC ACID
C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF NATURALLY OCCURRING SUBSTANCES .64. STRUCTURE OF MORONIC ACID
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DOI：
10.1021/jo01329a053
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发表时间：
1979-01-01
影响因子：
3.6
通讯作者：
WENKERT, E
中科院分区：
文献类型：
--
作者：
MAJUMDER, PL;MAITI, RN;WENKERT, E
将酯(4.12g，20.0mmol)在30mL乙醚中的溶液在10分钟内添加到剧烈搅拌的0.83g(0.12g原子，6.0当量)锂在250mL氨中的蓝色溶液中。在另外搅拌2小时期间蓝色持续存在。用氯化铵猝灭反应，让氨逸出，并添加50mL水和50mL乙醚。将两相混合物搅拌30分钟并分离。水相用三份20mL乙醚萃取。将合并的乙醚层用两份50mL的水洗涤，用无水MgSO 4 干燥，并浓缩，蒸馏后得到1.80g(88.2％)(6)(a)E.Wenkert和B.G.Jackson，J.Am。化学。 Soc.，80, 217 (1958)；(b) ML Meyer 和 A。 S.莱文森，J.Org。 Chem., 28, 2184 (1963)。(7) 苯甲酸钠在不添加质子的情况下淬灭金属-氨反应：SS Hall, S. D. Lipsky, and G. H. Small, Tetrahedron Lett., 1853 (1971)； SS Hall、S.D. Lipsky、FJ McEnroe 和 A. P. Bartels，J. Org。化学，36, 2588 (1971)。
A solution of the ester (4.12 g, 20.0 mmol) in 30 mL of ether was added over a 10-min period to a vigorously stirred blue solution of 0.83 g (0.12 g-atom, 6.0 equiv) of lithium in 250 mL of ammonia. Theblue color persisted during 2 h of additional stirring. The reaction was quenched with ammonium chloride, the ammonia was allowed to escape, and 50 mL ofwater and 50 mL of ether were added. The two-phase mixture was stirred for 30 min and separated. The aqueous phase was extracted with three 20-mL portions of ether. The combined ether layers were washed with two 50-mL portions of water, dried over anhydrous MgS04, and concentrated to give, after distillation, 1.80 g (88.2%)(6)(a) E. Wenkert and B. G. Jackson, J. Am. Chem. Soc., 80, 217 (1958);(b) ML Meyer andA. S. Levinson, J. Org. Chem., 28, 2184 (1963).(7) Sodium benzoate quenches metal-ammonia reactions without the addition of a proton: SS Hall, S. D. Lipsky, and G. H. Small, Tetrahedron Lett., 1853 (1971); SS Hall, S. D. Lipsky, FJ McEnroe, and A. P. Bartels, J. Org. Chem., 36, 2588 (1971).