氯碘甲烷 → 2-[2-(三氟甲基)苯基]环氧乙烷

HRID 2062

反应方程式

HRID 2062 反应方程式
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([CH:9]=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.I[CH2:14]Cl.C[Li]>O1CCCC1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][O:10]1

参与物

5

反应物 3

HCID 11644氯碘甲烷HCID 123067邻三氟甲基苯甲醛HCID 178418348HCID 178418348，化合物

产物 1

HCID 139032672-[2-(三氟甲基)苯基]环氧乙烷

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
-78 °C

实验过程

α,α,α-trifluoro-o-tolualdehyde (3 g) was dissolved in anhydrous tetrahydrofuran and cooled to -78° C., iodochloromethane (1.38 ml) was then added, followed by methyllithium (1.5M complexed with lithium bromide) (12 ml) added over 5 minutes. The reaction was left to warm up to room temperature overnight. The reaction was quenched using saturated ammonium chloride solution and extracted using diethyl ether (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to afford a brown oil. Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane afforded a colourless oil (1.1 g). 1H NMR (250 MHz, CDCl3) δ2.61-2.71 (1H, dd), 3.14-3.25 (1H, dd), 4.17-4.27 (1H, m), 7.33-7.70 (5H, m).

后处理

  1. additionadded over 5 minutes
  2. waitThe reaction was left
  3. temperatureto warm up to room temperature overnight
  4. customThe reaction was quenched
  5. extractionextracted
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto afford a brown oil
  10. customPurification on flash silica
  11. washeluted with 100% hexane up to 5% EtOAC in hexane

来源与证据

ORD记录
ord-622fcecd2a0b4607a07fac649d6051df
来源数据集
uspto-grants-1998_03
专利号
US05728695

关联笔记

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