Sodium Iodide → [(3-Hydroxyphenyl)(2-iodoethoxy)methylene]adamantane

HRID 964823Notes

Reaction equation

HRID 964823 reaction equation
[I-:1].[Na+].Cl[CH2:4][CH2:5][O:6][C:7](=[C:15]1[CH:22]2[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:24][CH:16]1[CH2:17]3)[CH2:21]2)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1.C(OCC)(=O)C.CCCCCC>CC(C)=O>[OH:14][C:10]1[CH:9]=[C:8]([C:7](=[C:15]2[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]2[CH2:17]4)[CH2:21]3)[O:6][CH2:5][CH2:4][I:1])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 15158794[(2-Chloroethoxy)(3-hydroxyphenyl)methylene]adamantaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 15158795[(3-Hydroxyphenyl)(2-iodoethoxy)methylene]adamantaneYield 102.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

##STR36## Sodium iodide (14.0 g, 0.09 mol) and [(2-chloroethoxy)(3-hydroxyphenyl)methylene]adamantahe 8 (3.0 g, 0.009 mol) were dissolved in dry acetone and refluxed for 6 days. The reaction was followed by TLC analysis (ethyl acetate/hexane, 10:90) 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 alkene 9 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 Hz), 3.35 (bs, 1H), 3.69 (t, 2H, J=7.1 Hz), 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); MS exact mass:calcd. 410.0744, found 410.0744.

Workup

  1. temperaturerefluxed for 6 days
  2. customafter the completion of reaction, solvent
  3. customwas evaporated
  4. customto obtain a white solid
  5. washThis solid was washed with methylene chloride several times
  6. washthe combined organic layers were again washed with water
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-22f5ed844858485a84e4e5b34dbd1c85
Source dataset
uspto-grants-1998_06
Patent number
US05770743

Reaction notes

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