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

HRID 15492ノート

反応式

HRID 15492 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-ecb997b2c8a34a65b93c81a56497c052
出典データセット
uspto-grants-2010_06
特許番号
US07732617B2

反応ノート

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