反应 #5446

反应方程式

diisopropyl ethyl amine

Triethyl orthoformate

product

4-Bromo-7-methoxy-2,3-dihydro-1H-inden-1-one

BF3.Et2O

→

white solid

4-Bromo-7-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxaldehyde diethy acetal

溶剂

methylene chloride

methylene chloride

反应条件

后处理

1. 1
   温度cooled to -78° C
2. 2
   温度The reaction was then warmed to -15° C. for 2 h
3. 3
   其他quenched in 5% NaHCO3 solution
4. 4
   萃取extracted with methylene chloride
5. 5
   洗涤The organic extracts were washed with brine
6. 6
   干燥dried (MgSO4)
7. 7
   其他the solvent removed
8. 8
   其他The crude product was triturated with cold hexane
9. 9
   其他the crystalline product collected

实验过程

Triethyl orthoformate (16.5 ml) was cooled to -30° C. and 15.0 ml BF3.Et2O in 50 ml methylene chloride was added. The reaction was warmed to 0° C. for 15 min, and then cooled to -78° C. To the reaction was added 12.05 g of the product from Example 34 in 50 ml methylene chloride, followed by dropwise addition of 19.4 ml diisopropyl ethyl amine. The reaction was then warmed to -15° C. for 2 h, then quenched in 5% NaHCO3 solution and extracted with methylene chloride. The organic extracts were washed with brine, dried (MgSO4), and the solvent removed. The crude product was triturated with cold hexane, and the crystalline product collected to yield 14.60 g of a white solid, mp: 76°-8° C. NMR (CDCl3) δ 1.05 (t, 3H), 1.27 (t, 3H), 3.03 (m, 2 H), 3.30 (m, 1H), 3.43-3.80 (m, 4H), 3.95 (s, 3H), 5.00 (d, 1H), 6.71 (d, 1H), 7.63 (d, 1H).

来源