反応 #5446

反応方程式

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

溶媒

methylene chloride

methylene chloride

反応条件

後処理

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
   その他quenched in 5% NaHCO3 solution
4. 4
   抽出extracted with methylene chloride
5. 5
   洗浄The organic extracts were washed with brine
6. 6
   乾燥dried (MgSO4)
7. 7
   その他the solvent removed
8. 8
   その他The crude product was triturated with cold hexane
9. 9
   その他the crystalline product collected

実験手順

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).

出典