Reacción #81039

Ecuación de reacción

Sodium iodide

[(2-chloroethoxy)(3-hydroxyphenyl)methylene]adamantane

ethyl acetate hexane

→

product

Rendimiento 102.9%

[(3-Hydroxyphenyl)(2-iodoethoxy)methylene]adamantane

Rendimiento 102.9%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 6 days
2. 2
   Otroafter the completion of reaction, solvent
3. 3
   Otrowas evaporated
4. 4
   Otroto obtain a white solid
5. 5
   LavadoThis solid was washed with methylene chloride several times
6. 6
   Lavadothe combined organic layers were again washed with water
7. 7
   SecadoThe organic layer was dried over MgSO4
8. 8
   Concentraciónconcentrated

Procedimiento

Sodium iodide (14.0 g, 0.09 mol) and [(2-chloroethoxy)(3-hydroxyphenyl)methylene]adamantane (3.0 g, 0.009 mol) were dissolved in dry acetone and refluxed for 6 days. The reaction was followed by TLC analysis (silica gel, 10% ethyl acetate/hexane) and after the completion of reaction, solvent was evaporated to obtain a white solid. This solid was washed with methylene chloride several times and the combined organic layers were again washed with water. The organic layer was dried over MgSO4 and concentrated to give 3.8 g (100%) of product as an oily material: 1H NMR (CDCl3) δ 1.78-1.97 (m, 12H), 2.64 (bs, 1H), 3.19 (t, 2H, J=7.1 MHz), 3.35 (bs, 1H), 3.69 (t, 2H, J=7.1 MHz), 6.75-7.21 (m, 4H); 13C NMR (CDCl3) δ 2.40, 28.13, 30.41, 32.33, 36.99, 38.86, 39.09, 69.74, 114.86, 116.00, 121.79, 129.28, 133.37, 136.42, 140.51, 155.66. MS m/e (rel intensity) 410 (42), 256 (19), 227 (75), 155 (18), 121 (100), 107 (32), 93 (28), 79 (14), 65 (16); Exact mass: calcd 410.0744, found: 410.0744. ##STR32##

Fuente