Imidazole → 4-(t-Butyldiphenylsilyloxy)-1-methyl-1-butanol

HRID 748693

反応式

HRID 748693 の反応式
[CH2:1]([OH:7])[CH2:2][CH2:3][CH:4]([OH:6])[CH3:5].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)C>CN(C)C=O>[Si:17]([O:7][CH2:1][CH2:2][CH2:3][CH:4]([CH3:5])[OH:6])([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 3283Diethyl EtherHCID 79083Pentane-1,4-diolHCID 94078tert-Butyldiphenylchlorosilane

生成物 1

HCID 230285714-(t-Butyldiphenylsilyloxy)-1-methyl-1-butanol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In N,N-dimethylformamide (200 ml) were dissolved 1,4-pentanediol (10.0 g, 96.0 mmol) and imidazole (6.6 g, 96.9 mmol). Under ice cooling, t-butyl chlorodiphenylsilane (25.2 ml, 96.4 mmol) was added dropwise. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 days. To the reaction mixture was added diethyl ether, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate. After filtration, the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (32.0 g, 97%) was obtained as a colorless oil.

後処理

  1. additionAfter completion of the dropwise addition
  2. washby washing with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe residue obtained
  6. concentrationby concentrating the filtrate under reduced pressure
  7. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (32.0 g, 97%)
  8. customwas obtained as a colorless oil

出典と根拠

ORDレコード
ord-70b62e78ab69429c94b4d30757a4585a
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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