Carbonic acid sodium salt (1:2) → Ethyl 3-(3-phenylphenyl)-2-propenoate

HRID 440954

反应方程式

HRID 440954 反应方程式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:15]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参与物

5

反应物 3

HCID 10340Carbonic acid sodium salt (1:2)HCID 66827苯硼酸HCID 568440NULL

产物 1

HCID 54054055Ethyl 3-(3-phenylphenyl)-2-propenoate收率 110.6%

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

实验过程

A stirred mixture of 11.0 grams (0.043 mole) of ethyl 3-(3-bromophenyl)-2-propenoate, 5.8 grams (0.047 mole) of phenylboronic acid, 0.25 gram (catalyst) of tetrakis-(triphenylphosphine)palladium(0), and 54.0 mL (0.110 mole) of a 2M solution of aqueous sodium carbonate in 100 mL of toluene was heated at reflux during a two hour period. After this time the reaction mixture was cooled, and the aqueous layer was separated. The toluene layer was washed with two 100 mL portions of water and then with 100 mL of an aqueous solution saturated with sodium chloride. The toluene layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 12.0 grams of ethyl 3-(3-phenylphenyl)-2-propenoate. The NMR spectrum was consistent with the proposed structure.

后处理

  1. temperaturewas heated
  2. temperatureat reflux during a two hour period
  3. temperatureAfter this time the reaction mixture was cooled
  4. customthe aqueous layer was separated
  5. washThe toluene layer was washed with two 100 mL portions of water
  6. dry with materialThe toluene layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

来源与证据

ORD记录
ord-43d4695caea04e73bf1b7383f4c9d4fc
来源数据集
uspto-grants-1996_05
专利号
US05521192

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