Tetrabutylammonium Fluoride → (R)-2-(9-(1H-1,2,3-Triazol-1-yl)nonyl)-2,5,7,8-tetramethylchroman-6-ol

HRID 15492노트

반응식

HRID 15492 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[C:28]([CH3:54])=[C:29]2[C:34](=[C:35]([CH3:38])[C:36]=1[CH3:37])[O:33][C@@:32]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][N:49]1[CH:53]=[CH:52][N:51]=[N:50]1)([CH3:39])[CH2:31][CH2:30]2)(C(C)(C)C)(C)C>C1COCC1>[N:49]1([CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][C@:32]2([CH3:39])[CH2:31][CH2:30][C:29]3[C:34](=[C:35]([CH3:38])[C:36]([CH3:37])=[C:27]([OH:26])[C:28]=3[CH3:54])[O:33]2)[CH:53]=[CH:52][N:51]=[N:50]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 25118684(R)-1-(9-(6-(tert-butyldimethylsilyloxy)-2,5,7,8-tetramethylchroman-2-yl)nonyl)-1H-1,2,3-triazole

생성물 1

HCID 25119043(R)-2-(9-(1H-1,2,3-Triazol-1-yl)nonyl)-2,5,7,8-tetramethylchroman-6-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of tetrabutylammonium fluoride (TBAF) (1M in THF, 250 μL) was added dropwise via syringe to a stirred solution of (R)-1-(9-(6-(tert-butyldimethylsilyloxy)-2,5,7,8-tetramethylchroman-2-yl)nonyl)-1H-1,2,3-triazole (65 mg, 0.126 mmol) in dry THF (5 ml). The mixture was stirred at room temperature for 30 minutes until starting material was not detected by TLC. The reaction was then quenched with 500 μL of 1N HCl and diluted with 25 ml of ether, to which an additional 10 ml of dH2O was added. The water phase was extracted again with ether (2×25 ml), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was chromatographed on silica gel (Et2O) to give the pure product (TLC Rf=0.49, EtOAc) as an off-white/yellow solid. (35 mg, 70%)

후처리

  1. customThe reaction was then quenched with 500 μL of 1N HCl
  2. additiondiluted with 25 ml of ether, to which an additional 10 ml of dH2O
  3. additionwas added
  4. extractionThe water phase was extracted again with ether (2×25 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was chromatographed on silica gel (Et2O)
  9. customto give the pure product (TLC Rf=0.49, EtOAc) as an off-white/yellow solid

출처 및 근거

ORD 기록
ord-ecb997b2c8a34a65b93c81a56497c052
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732617B2

반응 노트

불러오는 중…