反応式
[H-].[Na+].[N:3]1[C:8]([CH2:9][OH:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][OH:12].[C:13]([Si:17]([CH3:20])([CH3:19])Cl)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[Si:17]([O:12][CH2:11][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH2:9][OH:10])[N:3]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:20])[CH3:19]参加物
実験手順
To a solution of 60% NaH (1.45 g, 35.9 mmol) in DMF (60 mL), which was stirred and cooled with ice, was added a solution of 2,6-pyridinedimethanol (5.00 g, 35.9 mmol) in DMF (30 mL), and stirred for 1 hour at a room temperature under Ar atmosphere. To the mixture was added a solution of tert-butyldimethylchlorosilane (6.54 g, 43.3 mmol) in DMF (40 mL), and stirred for additional 12 hours. TLC was used to confirm there was no starting material in the reaction mixture. Then, the mixture was subjected to extraction with EtOAc and 10% NaHCO3 aq. The organic layer was washed with sat. NaClaq., dried over anhydrous Na2SO4, and evaporated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (Hex:EtOAc=5:1) to give 2-[(tert-butyldimethylsilyloxy)methyl]-6-hydroxymethylpyridine (1) (4.46 g, 49%) as a colorless oil.
後処理
- temperaturecooled with ice
- stirringstirred for additional 12 hours
- extractionThen, the mixture was subjected to extraction with EtOAc and 10% NaHCO3 aq. The organic layer
- washwas washed with sat. NaClaq
- dry with material, dried over anhydrous Na2SO4
- customevaporated under reduced pressure
- customto remove the solvent
- customThe residue was purified by silica gel column chromatography (Hex:EtOAc=5:1)
出典と根拠
- ORDレコード
- ord-c99b7afb08124b0783ebeb90ce15fc97
- 出典データセット
- uspto-grants-2014_01
- 特許番号
- US08633304B2
関連ノート
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