Tetrabutylammonium Fluoride Trihydrate → [(2-Chloroethoxy)(3-hydroxyphenyl)methylene]adamantane

HRID 964822Notes

Reaction equation

HRID 964822 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[C:20]2[CH:27]3[CH2:28][CH:23]4[CH2:24][CH:25]([CH2:29][CH:21]2[CH2:22]4)[CH2:26]3)[O:16][CH2:17][CH2:18][Cl:19])[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>C1COCC1>[Cl:19][CH2:18][CH2:17][O:16][C:15](=[C:20]1[CH:27]2[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2)[C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=1

Participants

5

Reactant 3

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 15158793[(3-tert-Butyldimethylsilyloxyphenyl) (2-chloroethoxy)methylene]adamantaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 15158794[(2-Chloroethoxy)(3-hydroxyphenyl)methylene]adamantaneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

##STR35## To a stirred solution of the tert-butyldimethylsilyl protected-alkene 7 shown above (2.0 g, 0.004 mol) in 5 mL of THF was added tetrabutylammonium fluoride trihydrate (TBAF, 1.4 g, 0.004 mol). The resulting solution was stirred for 10 minutes. TLC analysis (ethyl acetate/hexane, 20:80) indicated conversion to a new material. After evaporation of solvent, the crude product was washed with water and taken up in ether. The organic layer was dried over MgSO4 and evaporated to dryness. The oily material was chromatographed on silica gel using (ethyl acetate/hexane, 20:80) to give 1.3 g (100%) of alkene 8: 1H NMR (CDCl3) δ 1.81-1.96 (m, 12H), 2.67 (bs, 1H), 3.34 (bs, 1H), 3.55 (t, 2H, J=5.6 Hz), 3.69 (t, 2H, J=5.6 Hz), 6.77-7.19 (m, 4H); 13C NMR (CDCl3) δ 28.21, 30.24, 32.35, 37.08, 38.92, 39.19, 42.55, 69.05, 114.76, 116.05, 121.92, 129,31, 133.41, 136.62, 140.77, 155.64; MS m/e (rel intensity) 318 (100), 227 (19), 213 (24), 121 (92), 107 (29), 93 (37), 69 (21), 55 (36), 41 (40); MS exact mass: calcd. 318.1386, found 318.1383.

Workup

  1. customAfter evaporation of solvent
  2. washthe crude product was washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated to dryness
  5. customThe oily material was chromatographed on silica gel using (ethyl acetate/hexane, 20:80)

Sources & evidence

ORD record
ord-d56a2c96cbae4953a101dfa00512f1d8
Source dataset
uspto-grants-1998_06
Patent number
US05770743

Reaction notes

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