Imidazole → (1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

HRID 1672380

反応式

HRID 1672380 の反応式
[OH:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.C(N(CC)CC)C.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Si:20]([O:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

参加物

6

反応物 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

生成物 1

HCID 59000904(1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

1,1-Bis(hydroxymethyl)cyclopropane (1.0 g, 0.0098 mol), triethylamine (TEA) (2.0 mL, 0.015 mol), and 1H-imidazole (0.13 g, 0.0020 mol) were dissolved in anhydrous DCM (15 mL) and the solution was cooled to 0° C. A solution of tert-butyldimethylsilyl chloride (1.55 g, 0.0103 mol) in DCM (5 mL) was added drop-wise and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 and extracted with DCM (3×). The organic extract was dried (magnesium sulfate), filtered, and concentrated in vacuo. The crude product was identified by 1H NMR and used in the next step without further purification.

後処理

  1. temperatureto warm to RT
  2. customThe reaction was quenched with saturated aqueous NaHCO3
  3. extractionextracted with DCM (3×)
  4. extractionThe organic extract
  5. dry with materialwas dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customused in the next step without further purification

出典と根拠

ORDレコード
ord-6d2e0e14f7764fbca3d2d7096d880b54
出典データセット
uspto-grants-2011_08
特許番号
US07998959B2

関連ノート

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