Imidazole → 2-[2-(t-Butyldiphenylsilyloxy)ethylthio]ethanol

HRID 748792

反応式

HRID 748792 の反応式
[S:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].N1C=CN=C1.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].C(OCC)(=O)C>ClCCl>[Si:17]([O:4][CH2:3][CH2:2][S:1][CH2:5][CH2:6][OH:7])([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 5447ThiodiglycolHCID 8857Ethyl AcetateHCID 94078tert-Butyldiphenylchlorosilane

生成物 1

HCID 597508072-[2-(t-Butyldiphenylsilyloxy)ethylthio]ethanol収率 54.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In dichloromethane (200 ml) were dissolved 2,2′-thiodiethanol (10.0 g, 81.8 mmol) and imidazole (4.70 g, 69.0 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (15.0 ml, 57.7 mmol) at room temperature. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. After concentration under reduced pressure, diethyl ether was added to the residue. Then, the insoluble matter was filtered off. The residue obtained by concentrating the filtrate under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure, whereby the title compound (11.3 g, 31.3 mmol, 54%) was obtained as a colorless oil.

後処理

  1. additionAfter completion of the dropwise addition
  2. concentrationAfter concentration under reduced pressure, diethyl ether
  3. additionwas added to the residue
  4. filtrationThen, the insoluble matter was filtered off
  5. customThe residue obtained
  6. concentrationby concentrating the filtrate under reduced pressure
  7. customthe fraction obtained from the hexane

出典と根拠

ORDレコード
ord-b676ef213e204279a50daff62ebef92f
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

関連ノート

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