反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
PROCEDURE
实验过程
A mixture of a compound [7a] (80.0 g), palladium on carbon catalyst (16 g) and ethyl acetate (1.0 L) was stirred under hydrogen atmosphere at 150 psi for 3 hours at room temperature. The reaction mixture was then filtered and evaporated under reduced pressure. The oily residue was crystallized from a mixture of hexane and ethyl acetate 4:1 v/v to give 71.4 g (89% yield) of compound [9a], mp 103-105° C., [α]D20 −107° (c 1.0, MeCN). 1H NMR (CDCl3) δ: 8.03 (d, J=8 Hz, 2H); 7.60-7.67 (m, 4H); 7.36-7.48 (m, 3H); 7.14-7.24 (m, 5H); 5.20-5.30 (m, 1H); 5.00-5.15 (m, 1H); 4.50-4.70 (m, 1H), 3.89-3.95 (m, 1H); 3.66-3.72 (m, 1H); 3.45-3.50 (m, 1H). 13C NMR (CDCl3) δ: 20.1; 25.4; 28.7; 31.3; 31.9; 36.5; 43.5; 52.8; 63.0; 76.0; 80.1; 84.3; 97.8; 125.7; 127.1; 127.2; 128.1; 128.3; 128.4; 128.9; 130.1; 140.0; 142.4; 146.0; 165.8; 176.7. IR (KBr): 2990; 1771; 1707; 1608; 1277; 1181; 1110; 1026; 751; 698 cm−1.
WORKUP
后处理
- filtrationThe reaction mixture was then filtered
- customevaporated under reduced pressure
- customThe oily residue was crystallized from a mixture of hexane and ethyl acetate 4:1 v/v