Tetrabutylammonium Fluoride → [3-(Cyclopentylsulfanyl)phenyl]methanol

HRID 901632

反応式

HRID 901632 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([S:34][CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:29]=1)(C)C)(C)(C)C>C1COCC1>[CH:35]1([S:34][C:30]2[CH:29]=[C:28]([CH2:27][OH:26])[CH:33]=[CH:32][CH:31]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 66845801Tert-butyl([3-(cyclopentylthio)benzyl]oxy}dimethylsilane

生成物 1

HCID 66347770[3-(Cyclopentylsulfanyl)phenyl]methanol収率 92.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of tetrabutylammonium fluoride in THF (1M, 6 ml) was added to a solution of tert-butyl{[3-(cyclopentylthio)benzyl]oxy}dimethylsilane (1.09 g) in dry THF (10 ml). The solution was stirred for 18 h under nitrogen and the solvent was evaporated in vacuo. The residue was partitioned between dichloromethane and water. The organic phase was separated and washed with water. The organic phase was separated and the solvent evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with a stepped gradient of 10% to 100% dichloromethane-cyclohexane to give the title compound (0.65 g). LCMS RT=3.3 min.

後処理

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between dichloromethane and water
  3. customThe organic phase was separated
  4. washwashed with water
  5. customThe organic phase was separated
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with a stepped gradient of 10% to 100% dichloromethane-cyclohexane

出典と根拠

ORDレコード
ord-76117cad6b9640ef8967ae979cdfa5dc
出典データセット
uspto-grants-2008_04
特許番号
US07361787B2

関連ノート

読み込み中…