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

HRID 15492Notes

Reaction equation

HRID 15492 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%)

Workup

  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

Sources & evidence

ORD record
ord-ecb997b2c8a34a65b93c81a56497c052
Source dataset
uspto-grants-2010_06
Patent number
US07732617B2

Reaction notes

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