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

HRID 336326노트

반응식

HRID 336326 반응식
[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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3975e18fb11d431481c2c3a78d6f3bdc
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889669B2

반응 노트

불러오는 중…