反応 #67913

反応方程式

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

収率 83.1%

溶媒

CH2Cl2

CH2Cl2

H2O

反応条件

後処理

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

実験手順

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).

出典