Реакция #5446

Уравнение реакции

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

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   Температураcooled to -78° C
2. 2
   ТемператураThe reaction was then warmed to -15° C. for 2 h
3. 3
   Другоеquenched in 5% NaHCO3 solution
4. 4
   Экстракцияextracted with methylene chloride
5. 5
   ПромывкаThe organic extracts were washed with brine
6. 6
   Сушкаdried (MgSO4)
7. 7
   Другоеthe solvent removed
8. 8
   ДругоеThe crude product was triturated with cold hexane
9. 9
   Другоеthe crystalline product collected

Методика

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).

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