Tetrabutylammonium Fluoride → (5-((2-(2-(2-Methoxyethoxy)ethoxy)ethyl)(2-methyl-2-(methyldisulfanyl)propyl)amino)-1,3-phenylene)dimethanol

HRID 1615096Notes

Reaction equation

HRID 1615096 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[CH:29]=[C:30]([CH:49]=[C:50]([CH2:52][O:53][Si](C(C)(C)C)(C)C)[CH:51]=1)[N:31]([CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48])[CH2:32][C:33]([CH3:38])([S:35][S:36][CH3:37])[CH3:34])(C(C)(C)C)(C)C>C1COCC1>[CH3:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][N:31]([CH2:32][C:33]([CH3:38])([S:35][S:36][CH3:37])[CH3:34])[C:30]1[CH:29]=[C:28]([CH2:27][OH:26])[CH:51]=[C:50]([CH2:52][OH:53])[CH:49]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866712843,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-(2-methyl-2-(methyldisulfanyl)propyl)aniline

Product 1

HCID 86671285(5-((2-(2-(2-Methoxyethoxy)ethoxy)ethyl)(2-methyl-2-(methyldisulfanyl)propyl)amino)-1,3-phenylene)dimethanolYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1M in THF) (10.57 ml, 10.57 mmol) was added dropwise to stirring solution of 3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-(2-methyl-2-(methyldisulfanyl)propyl)aniline (3.5 g, 5.29 mmol) in anhydrous THF (65 ml) at 0° C. in an ice bath. Following addition the mixture was stirred at ambient temperature for two hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The extracts were washed with water and brine, dried with magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (MeOH/DCM) yielded (5-((2-(2-(2-methoxyethoxy)ethoxy)ethyl)(2-methyl-2-(methyldisulfanyl)propyl)amino)-1,3-phenylene)dimethanol (2 g, 87%). 1H NMR (400 Hz, CDCl3): δ 6.76 (s, 2H), 6.63 (s, 1H), 4.55 (s, 4H), 3.65-3.51 (m, 14H), 3.35 (s, 3H), 2.44 (s, 3H), 1.33 (s, 6H); 13C NMR (400 Hz, CDCl3): δ 149.0, 142.35, 114.0, 111.1, 71.98, 70.7, 70.6, 70.5, 67.6, 65.5, 59.75, 59.1, 53.9, 51.9, 26.6, 25.7, 20.75; MS (m/z). found 456.2 (M+Na)+. See FIG. 46.

Workup

  1. additionaddition the mixture
  2. customThe mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-796d1331035d4c9e9f415ac496680fd3
Source dataset
uspto-grants-2014_07
Patent number
US08765740B2

Reaction notes

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