N,N-二甲基甲酰胺 → Methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]propanoate

HRID 369447笔记

反应方程式

HRID 369447 反应方程式
C(=O)([O-])[O-].[K+].[K+].[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][C:15]=2[OH:22])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.CN(C)C=O.Cl[CH:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31]>C1(C)C=CC=CC=1>[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][C:15]=2[O:22][CH:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

参与物

6

反应物 4

HCID 6228N,N-二甲基甲酰胺HCID 11430碳酸钾HCID 286592-氯丙酸甲酯HCID 232864162-(Morpholin-4-ylmethyl)-5-ethylphenol

产物 1

HCID 15483901Methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]propanoate收率 84.5%

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

反应条件

温度
110 °C

实验过程

To a one liter round bottom flask equipped with a mechanical stirrer and a thermometer was added 157.13 grams (1.14 moles--1.3 equiv.) of potassium carbonate, followed by 215.27 grams (0.875 mole--1.0 equiv.) of 89.9% pure 2-(morpholin-4-ylmethyl)-5-ethylphenol, and 230 mL (%Wt/Vol. Phenol to Solvent--93.6%) of N,N-dimethylformamide. The mixture was vigorously stirred and heated to 110° C., and then 139.3 grams (1.14 moles--1.3 equiv.) of methyl 2-chloropropanoate was added during a one hour period. Upon completion of addition, the reaction mixture was analyzed by GC, which indicated the reaction was incomplete. The reaction mixture was heated at 110° C. for seven hours. After this time, the reaction mixture was again analyzed by GC, which indicated the reaction was complete. The reaction mixture was filtered, and the orange filtrate was kept under a nitrogen atmosphere for about 48 hours. After this time, the filtrate was concentrated under vacuum at 90° C. and 10 mm of mercury to yield a red, brown liquid. The liquid was taken up in 200 mL of toluene, and the resulting solution was washed with two 500 mL portions of an aqueous saturated sodium chloride solution. The organic layer was separated from the aqueous layer, dried with magnesium sulfate, and filtered. The filtrate was concentrated under vacuum at 90° C. and 10 mm of mercury, yielding 252.7 grams of 83.6% pure methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]propanoate (78.6% yield). The NMR spectrum was consistent with the proposed structure.

后处理

  1. customTo a one liter round bottom flask equipped with a mechanical stirrer
  2. additionUpon completion of addition
  3. temperatureThe reaction mixture was heated at 110° C. for seven hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationAfter this time, the filtrate was concentrated under vacuum at 90° C.
  6. custom10 mm of mercury to yield a red, brown liquid
  7. washthe resulting solution was washed with two 500 mL portions of an aqueous saturated sodium chloride solution
  8. customThe organic layer was separated from the aqueous layer
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under vacuum at 90° C.

来源与证据

ORD记录
ord-fe591173e53b4b3686fb1b1abfcc4683
来源数据集
uspto-grants-2000_10
专利号
US06136972

反应笔记

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