Tetrahydrofuran → Stannane, tributyl-3-furanyl-

HRID 21909

反応式

HRID 21909 の反応式
C([Li])CCC.[O:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.BrC1C=COC=1.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>CCCCCC>[O:6]1[CH:10]=[CH:9][C:8]([Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:7]1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 15096Tributyltin ChlorideHCID 891643-BromofuranHCID 178418339Butyllithium

生成物 1

HCID 11760097Stannane, tributyl-3-furanyl-

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-60 °C

実験手順

69.5 ml of a 1.6 molar solution of n-butyllithium in hexane are mixed with 60 ml of absolute tetrahydrofuran. The mixture is cooled to -60° C. and 10 ml of 3-bromofuran are added dropwise at such a rate that the internal temperature does not exceed -50° C.. When the addition is complete, the whole is stirred for 15 minutes at -60° C. and then 33.2 ml of tributyltin chloride are added dropwise, during the course of which the internal temperature is not allowed to exceed -50° C.. When the addition is complete, the reaction solution is allowed to come to -10° C. and is then stirred for one hour at that temperature. The solution is then carefully quenched with water. The aqueous phase is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over sodium sulphate. It is filtered off and the solvent is removed in vacuo. The crude product obtained is purified by distillation in a high vacuum. 30.14 g of (3-furanyl)tributylstannane are obtained in the form of a light-yellow oil (boiling point=100°-104° C. at 0.09 torr).

後処理

  1. customdoes not exceed -50° C.
  2. additionWhen the addition
  3. customto exceed -50° C.
  4. additionWhen the addition
  5. customto come to -10° C.
  6. stirringis then stirred for one hour at that temperature
  7. customThe solution is then carefully quenched with water
  8. extractionThe aqueous phase is extracted with ethyl acetate
  9. washThe organic phase is washed with saturated sodium chloride solution
  10. dry with materialdried over sodium sulphate
  11. filtrationIt is filtered off
  12. customthe solvent is removed in vacuo
  13. customThe crude product obtained
  14. distillationis purified by distillation in a high vacuum

出典と根拠

ORDレコード
ord-6be063efd36f4a1c8d76b87968f64262
出典データセット
uspto-grants-1995_06
特許番号
US05426102

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