tert-Butyldimethylsilyl chloride → 1-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-ol

HRID 633387

反応式

HRID 633387 の反応式
[CH3:1][C:2]([OH:6])([CH3:5])[CH2:3][OH:4].[CH3:7][C:8]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])[CH3:9]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:8]([Si:11]([CH3:13])([CH3:12])[O:4][CH2:3][C:2]([CH3:5])([OH:6])[CH3:1])([CH3:10])([CH3:9])[CH3:7]

参加物

5

反応物 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 684102-Methylpropane-1,2-diol

生成物 1

HCID 189346221-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-ol収率 84%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

2-Methylpropane-1,2-diol (1.08 g, 12.0 mmol, 1.0 equiv) in DCM (40 mL) under argon was cooled to 0° C. TEA (2.50 mL, 18.0 mmol, 1.5 equiv), DMAP (75.0 mg, 0.600 mmol, 0.05 equiv), and TBSCl (2.00 g, 13.2 mmol, 1.1 equiv) were added sequentially, and the reaction was allowed to warm up to ambient temperature overnight. Complete conversion of reactant to product was confirmed by TLC eluted with EtOAc and visualized with KMnO4. The solvent was removed in vacuo, and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc 2×, and the combined organics were dried with Na2SO4, filtered, and concentrated to provide 1-(tertbutyldimethylsilyloxy)-2-methylpropan-2-ol (2.05 g, 84%) as a light brown oil that was used without further purification.

後処理

  1. washeluted with EtOAc
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc 2×
  5. dry with materialthe combined organics were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ec92d2b197034b40b36cef6e6ddb730f
出典データセット
uspto-grants-2016_04
特許番号
US09321763B2

関連ノート

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