tert-Butyldimethylsilyl chloride → 2-[(Tert-butyldimethylsilyloxy)methyl]benzylalcohol

HRID 1854676ノート

反応式

HRID 1854676 の反応式
[C:1]1([CH2:9][OH:10])[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C(N(CC)C(C)C)(C)C.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>ClCCl.C(OCC)C>[Si:20]([O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][OH:10])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

参加物

6

反応物 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 691531,2-BenzenedimethanolHCID 81531Diisopropylethylamine

生成物 1

HCID 108484452-[(Tert-butyldimethylsilyloxy)methyl]benzylalcohol収率 57%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1,2-benzenedimethanol (500 mg, 3.62 mmol), N,N-diisopropylethylamine (0.76 mL, 4.4 mmol) in 3.6 mL of dichloromethane was added tert-butyldimethylsilyl chloride (573 mg, 3.80 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 1 day. The reaction mixture was diluted with diethyl ether, and the solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15) to obtain 2-[(tert-butyldimethylsilyloxy)methyl]benzylalcohol as a colorless oil (520 mg, 57%).

後処理

  1. washthe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15)

出典と根拠

ORDレコード
ord-bddca0c5791b43dc9aaa9ded136ef32a
出典データセット
uspto-grants-2015_02
特許番号
US08962674B2

反応ノート

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