Ethyl 2-butynoate → (E)-3-(2,6-difluoro-3-methoxy-phenoxy)-but-2-enoic acid ethyl ester

HRID 19122노트

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HRID 19122 반응식
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[OH:11].[CH2:12]([O:14][C:15](=[O:19])[C:16]#[C:17][CH3:18])[CH3:13].N12CCCN=C1CCCCC2>O1CCCC1>[CH2:12]([O:14][C:15](=[O:19])/[CH:16]=[C:17](/[O:11][C:3]1[C:4]([F:10])=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[F:1])\[CH3:18])[CH3:13]

참가 물질

5

반응물 3

HCID 78043Ethyl 2-butynoateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 36828622,6-Difluoro-3-methoxyphenol

생성물 1

HCID 66894753(E)-3-(2,6-difluoro-3-methoxy-phenoxy)-but-2-enoic acid ethyl ester수율 76.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a stirred mixture of 2,6-difluoro-3-methoxy-phenol (5.00 g, 0.031 mol) and ethyl-2-butynoate (7.00 g, 0.062 mol) in tetrahydrofuran (40 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.76 g, 0.031 mol) in tetrahydrofuran (10 mL) slowly. After addition was complete the mixture was stirred at reflux overnight. 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 purified by ISCO column chromatography (Teledyne Isco RediSep Flash Column 120 g, 0% to 15%) ethyl acetate/hexanes which afforded (E)-3-(2,6-difluoro-3-methoxy-phenoxy)-but-2-enoic acid ethyl ester (6.42 g, 76%) as a colorless oil.

후처리

  1. additionAfter addition
  2. temperatureat reflux overnight
  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 purified by ISCO column chromatography (Teledyne Isco RediSep Flash Column 120 g, 0% to 15%) ethyl acetate/hexanes which

출처 및 근거

ORD 기록
ord-2cddb078f51c43a7951c6dc128202acb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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