O-Cresol → (E)-3-o-tolyloxy-but-2-enoic acid ethyl ester

HRID 19126

반응식

HRID 19126 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]([O:11][C:12](=[O:16])[C:13]#[C:14][CH3:15])[CH3:10].N12CCCN=C1CCCCC2>O1CCCC1>[CH2:9]([O:11][C:12](=[O:16])/[CH:13]=[C:14](/[O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])\[CH3:15])[CH3:10]

참가 물질

5

반응물 3

HCID 335O-CresolHCID 78043Ethyl 2-butynoateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 66894216(E)-3-o-tolyloxy-but-2-enoic acid ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred mixture of 2-methyl-phenol (4.90 g, 0.045 mol) and ethyl-2-butynoate (10.1 g, 0.09 mol) in tetrahydrofuran (15 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (6.80 g, 0.045 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 crude product, (E)-3-o-tolyloxy-but-2-enoic acid ethyl ester, was obtained as a brown oil (6.45 g, 65%) 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

출처 및 근거

ORD 기록
ord-d62cd1908464458c8d54b3ca4efbb353
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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