Potassium Carbonate → (R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol

HRID 1895529ノート

反応式

HRID 1895529 の反応式
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:14][CH2:15][C@H:16]([OH:24])[CH2:17][C:18]#[C:19][Si](C)(C)C)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>CO>[Si:7]([O:14][CH2:15][C@H:16]([OH:24])[CH2:17][C:18]#[CH:19])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 53308767(R)-1-((tert-Butyldimethylsilyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

生成物 1

HCID 86667884(R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol収率 80%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Potassium carbonate (2.14 g, 15.5 mmol) was added to a solution of (R)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol (3 g, 10.6 mmol) in methanol (100 mL) and the mixture stirred at room temperature for 8 hours. The solvent was removed under reduced pressure and aqueous ammonium chloride solution (100 mL) was added to the resulting oil. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude material was purified by flash chromatography (biotage) using a gradient of EtOAc in hexane to afford (R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol (1.81 g, 8.44 mmol, 80%).

後処理

  1. customThe solvent was removed under reduced pressure and aqueous ammonium chloride solution (100 mL)
  2. additionwas added to the resulting oil
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography (biotage)

出典と根拠

ORDレコード
ord-56195a7f67f04d11aeea6851bc14b164
出典データセット
uspto-grants-2013_08
特許番号
US08513443B2

反応ノート

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