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

HRID 1779381

反応式

HRID 1779381 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-611cdcd27dc441a3bbb9eb12fa2b5a4f
出典データセット
uspto-grants-1997_05
特許番号
US05627189

関連ノート

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