Sodium Carbonate → Ethyl 3-(3-phenylphenyl)-2-propenoate

HRID 1779381

반응식

HRID 1779381 반응식
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

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 568440Ethyl 3-(3-bromophenyl)prop-2-enoate

생성물 1

HCID 54054055Ethyl 3-(3-phenylphenyl)-2-propenoate수율 110.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-611cdcd27dc441a3bbb9eb12fa2b5a4f
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05627189

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