Tetrabutylammonium Fluoride → HCID 22496024、化合物

HRID 1816007ノート

反応式

HRID 1816007 の反応式
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:43][Si](C(C)(C)C)(C)C)([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)C#N)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[O:43])=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 22496050HCID 22496050、化合物

生成物 1

HCID 22496024HCID 22496024、化合物収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of TBAF in THF (1.0 M, 2.2 mL, 2.2 mmole) was added dropwise to a solution of (±)-3-(4-benzyloxyphenyl)-2-(ter-butyldimethylsilyloxy)-2-(pyridin-3-yl)propionitrile (769 mg, 1.73 mmole) in dry THF (10 mL) at −15° C. After 30 min, the reaction was partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with H2O, dried (MgSO4), filtered through a plug of silica gel, and concentrated to afford impure title compound (492 mg, 94%) as a yellow solid: MS (ES) m/e 304 (M+H)+. This material was used without further purification.

後処理

  1. customthe reaction was partitioned between EtOAc and H2O
  2. customThe layers were separated
  3. washthe organic layer was washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through a plug of silica gel
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8590528ae1ec47899148221c54bfa954
出典データセット
uspto-grants-2005_04
特許番号
US06881736B1

反応ノート

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