海萝胶 → 3-Propyloxirane-2-carboxylic acid

HRID 391487

反应方程式

HRID 391487 反应方程式
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH3:6].C(=O)(O)[O-:10].[Na+].OOS([O-])=O.[K+].Cl>[Na+].[Na+].C(N(CC(O)=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=O.CC(C)=O.O>[CH2:4]([CH:3]1[O:10][CH:2]1[C:1]([OH:8])=[O:7])[CH2:5][CH3:6]

参与物

8

反应物 4

HCID 313海萝胶HCID 516892碳酸氢钠2 次HCID 5282707反式-2-己烯酸2 次HCID 23707502Potassium hydroxy sulfite

产物 1

HCID 134405333-Propyloxirane-2-carboxylic acid收率 76%

试剂、催化剂与溶剂 3

HCID 180丙酮溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 13020083乙二胺四乙酸二钠溶剂

反应条件

温度
0 °C

实验过程

A flask equipped with an overhead stirrer, thermometer and addition funnel was placed under a nitrogen atmosphere then charged with trans-2-hexenoic acid (69.8 g, 611 mmol), water (420 mL) and acetone (420 mL). Sodium bicarbonate (NaHCO3, 224 g, 2.66 mol) was then added portion-wise keeping the reaction temperature at 25±5° C. Once all of the sodium bicarbonate had been added, a solution of OXONE® (454 g, 738 mmol) in 4×10−4 M ethylenediaminetetraacetic acid disodium salt dehydrate (Na2EDTA; 1.32 L) was charged to the addition funnel and added over 90 minutes keeping the reaction temperature at 25±5° C. and the pH between 9.5 and 7.5. The reaction mixture was then allowed to stir for 16 h, after which time no (E)-hex-2-enoic acid was observed by HPLC analysis. The mixture was cooled to 0±5° C., acidified to pH 2 with 6 N HCl (515 mL, 2.8 mol) and extracted with ethyl acetate (EtOAc; 3×250 mL). The combined organic phases were dried over sodium sulfate (Na2SO4), filtered then concentrated under reduced pressure to provide the title compound (60.4 g, 76%) as a yellow oil.

后处理

  1. customA flask equipped with an overhead stirrer
  2. additionthermometer and addition funnel
  3. customat 25±5° C
  4. additionadded over 90 minutes
  5. customat 25±5° C.
  6. extractionextracted with ethyl acetate (EtOAc; 3×250 mL)
  7. dry with materialThe combined organic phases were dried over sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. concentrationthen concentrated under reduced pressure

来源与证据

ORD记录
ord-2fbbc111b258439e998f44b120c59e70
来源数据集
uspto-grants-2013_02
专利号
US08383858B2

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