结晶氯化高锡 → (E)-1-methoxy-10-methyl-12-pentylazacyclododec-9-en-2-one

HRID 2205259笔记

反应方程式

HRID 2205259 反应方程式
[CH2:1]=[C:2]([CH:4]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:12])[CH3:3].[CH3:13][O:14][N:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH3:13][O:14][N:15]1[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][C:2]([CH3:1])=[CH:4][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:12]

参与物

5

反应物 3

HCID 24287结晶氯化高锡HCID 551988Hexanal O-methyl oximeHCID 895256422-(Prop-1-en-2-yl)cyclooctanone

产物 1

HCID 131735807(E)-1-methoxy-10-methyl-12-pentylazacyclododec-9-en-2-one收率 89.3%

试剂、催化剂与溶剂 1

HCID 111,2-二氯乙烷溶剂

实验过程

An argon flushed three-necked flask which was cooled by an ice-water bath was charged with 2-(prop-1-en-2-yl)cyclooctanone (1.50 g, 9.02 mmol), hexanal O-methyl oxime (1.56 g, 13.53 mmol), and SnCl4 (2.35 g, 9.02 mmol) in 1,2-dichloroethane (90 ml). The mixture was stirred for 2 days at room temperature. The completion of reaction was checked by GC analysis of reaction aliquots quenched with a solution of saturated NaHCO3 in water. The reaction mixture was quenched with sat. aqueous NaHCO3 solution (50 mL). The organic phase was separated and the aqueous layer was extracted with MTBE three times. The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated in vacuo. The crude product was purified by distillation to give the title product as a yellow oily liquid (2.38 g, 89%). E isomers>98%.

后处理

  1. temperatureAn argon flushed three-necked flask which was cooled by an ice-water bath
  2. customThe completion of reaction
  3. customwas checked by GC analysis of reaction aliquots
  4. customquenched with a solution of saturated NaHCO3 in water
  5. customThe reaction mixture was quenched with sat. aqueous NaHCO3 solution (50 mL)
  6. customThe organic phase was separated
  7. extractionthe aqueous layer was extracted with MTBE three times
  8. washThe combined organic layers were washed with brine (30 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. distillationThe crude product was purified by distillation

来源与证据

ORD记录
ord-b47a7496db54438c81512930bc6aa263
来源数据集
uspto-grants-2016_06
专利号
US09371262B2

反应笔记

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