3-Cyanophenol → (E)-3-(3-cyano-phenoxy)-but-2-enoic acid methyl ester

HRID 19152

반응식

HRID 19152 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][O:11][C:12](=[O:16])[C:13]#[C:14][CH3:15].N12CCCN=C1CCCCC2>O1CCCC1>[CH3:10][O:11][C:12](=[O:16])/[CH:13]=[C:14](/[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)\[CH3:15]

참가 물질

5

반응물 3

HCID 133943-CyanophenolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141019Methyl but-2-ynoate

생성물 1

HCID 66895047(E)-3-(3-cyano-phenoxy)-but-2-enoic acid methyl ester수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred mixture of 3-hydroxy-benzonitrile (3.30 g, 0.028 mol) and methyl-2-butynoate (5.40 g, 0.055 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.20 g, 0.028 mol) slowly. After addition was complete the mixture was stirred at reflux for 6 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue dried under high vacuum which afforded (E)-3-(3-cyano-phenoxy)-but-2-enoic acid methyl ester as an oil (4.60 g, 76%) and used without further purification.

후처리

  1. additionAfter addition
  2. temperatureat reflux for 6 h
  3. customwas removed in vacuo
  4. additionthe residue was diluted in diethyl ether
  5. washwashed first with 1N aqueous hydrochloric acid
  6. dry with material10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customevaporated
  9. customthe residue dried under high vacuum which

출처 및 근거

ORD 기록
ord-fb3e6c940794475996d3ab2a68d25e21
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

연결된 노트

불러오는 중…