Sodium hydride → (1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

HRID 906436

反応式

HRID 906436 の反応式
[C:1]1([CH2:6][OH:7])([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11]>COCCOC.O>[Si:14]([O:5][CH2:4][C:1]1([CH2:6][OH:7])[CH2:3][CH2:2]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

生成物 1

HCID 59000904(1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol収率 70.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
20 °C

実験手順

A solution of cyclopropane-1,1-diyldimethanol (3.7 g) dissolved in ethylene glycol dimethyl ether (50 mL) was treated with 60% sodium hydride (1.449 g) at 0° C. under nitrogen. The resulting mixture was stirred at 20° C. for 1 h, treated with tert-butylchlorodimethylsilane (5.46 g) and stirred at room temperature overnight. The reaction mixture was diluted with water (250 mL), and extracted with ethyl acetate (2×250 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography, elution 100% DCM). Pure fractions were evaporated to dryness to afford the subtitle compound (5.50 g) as an oil.

後処理

  1. stirringstirred at room temperature overnight
  2. extractionextracted with ethyl acetate (2×250 mL)
  3. dry with materialThe organic was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified
  8. wash(SiO2 chromatography, elution 100% DCM)
  9. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-3550cdff5c8e47f3abd24d89c79ace22
出典データセット
uspto-grants-2011_09
特許番号
US08012980B2

関連ノート

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