2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(1-Chlorobut-3-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 850872ノート

反応式

HRID 850872 の反応式
[Cl:1][CH:2](Cl)[B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1.[CH2:13]([Mg]Br)[CH:14]=[CH2:15]>O1CCCC1>[Cl:1][CH:2]([B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1)[CH2:15][CH:14]=[CH2:13]

参加物

4

反応物 2

HCID 110420412-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178455850HCID 178455850、化合物

生成物 1

HCID 126805082-(1-Chlorobut-3-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 70.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2 g (9.48 mmol) of 2-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were dissolved in 30 ml of tetrahydrofuran and the solution was cooled under a nitrogen atmosphere to -78° C. 9.5 ml (9.5 mmol) of 1M allylmagnesium bromide were added dropwise and the solution was stirred at room temperature for 18 hours. The solution was partitioned between ethyl acetate, saturated sodium chloride solution and 2M hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate and the organic layers were combined and dried over anhydrous sodium sulphate. After filtration and evaporation the oil obtained was distilled to give 1.45 g of 2-(1 (RS)-chloro-3-butenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; b.p. 53° C./0.4 mm Hg.

後処理

  1. customThe solution was partitioned between ethyl acetate, saturated sodium chloride solution and 2M hydrochloric acid solution
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationAfter filtration and evaporation the oil
  5. customobtained
  6. distillationwas distilled

出典と根拠

ORDレコード
ord-02fa0e6fb3a345e8a448c783004dfe8f
出典データセット
uspto-grants-2000_01
特許番号
US06018020

反応ノート

読み込み中…