반응 #5446

반응 방정식

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

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   온도cooled to -78° C
2. 2
   온도The reaction was then warmed to -15° C. for 2 h
3. 3
   기타quenched in 5% NaHCO3 solution
4. 4
   추출extracted with methylene chloride
5. 5
   세척The organic extracts were washed with brine
6. 6
   건조dried (MgSO4)
7. 7
   기타the solvent removed
8. 8
   기타The crude product was triturated with cold hexane
9. 9
   기타the crystalline product collected

실험 절차

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).

출처