反応 #81039

反応方程式

Sodium iodide

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

ethyl acetate hexane

→

product

収率 102.9%

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

収率 102.9%

溶媒

acetone

反応条件

後処理

1. 1
   温度refluxed for 6 days
2. 2
   その他after the completion of reaction, solvent
3. 3
   その他was evaporated
4. 4
   その他to obtain a white solid
5. 5
   洗浄This solid was washed with methylene chloride several times
6. 6
   洗浄the combined organic layers were again washed with water
7. 7
   乾燥The organic layer was dried over MgSO4
8. 8
   濃縮concentrated

実験手順

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##

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