반응 #81039

반응 방정식

Sodium iodide

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

ethyl acetate hexane

→

product

수율 102.9%

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

수율 102.9%

용매

acetone

반응 조건

후처리

1. 1
   온도refluxed for 6 days
2. 2
   기타after the completion of reaction, solvent
3. 3
   기타was evaporated
4. 4
   기타to obtain a white solid
5. 5
   세척This solid was washed with methylene chloride several times
6. 6
   세척the combined organic layers were again washed with water
7. 7
   건조The organic layer was dried over MgSO4
8. 8
   농축concentrated

실험 절차

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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