反应 #67913

反应方程式

2-allyloxymethyl-3-methoxy-benzoic acid N′-tert-butyl-hydrazide

3,5-dimethylbenzoyl chloride

K2CO3

→

3,5-dimethyl-benzoic acid N′-(2-allyloxymethyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide

收率 83.1%

溶剂

CH2Cl2

CH2Cl2

H2O

反应条件

后处理

1. 1
   workup.ADDITIONThe reaction mixture was diluted
2. 2
   其他partitioned
3. 3
   其他the organic phase was dried
4. 4
   其他solvent was removed in vacuio
5. 5
   其他The product was purified by silica gel chromatography
6. 6
   洗涤eluting in 25% ethyl acetate

实验过程

To a flask containing 2.0 g (0.0068 mol) of 2-allyloxymethyl-3-methoxy-benzoic acid N′-tert-butyl-hydrazide dissolved in 15 mL of CH2Cl2, was added 1.27 g (0.0075 mol) of 3,5-dimethylbenzoyl chloride in 10 mL of CH2Cl2 and 2.84 g of K2CO3 (0.02 mol) in 30 mL of H2O. The mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted and partitioned, and the organic phase was dried and solvent was removed in vacuio. The product was purified by silica gel chromatography; eluting in 25% ethyl acetate:hexane fractions, to yield 2.40 g of pure 3,5-dimethyl-benzoic acid N′-(2-allyloxymethyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.2 (t, 1H) 7.1 (s, 1H), 7.05 (d, 2H), 6.95 (m, 2H), 5.9 (m, 1H), 5.2-5.3 (q, 2H), 4.5 (d, 2H), 3.9 (m, 2H), 3.80 (s, 3H), 2.245 (s, 6H), 1.547 (s, 9H).

来源