Acetic Acid → HCID 54165322, 화합물

HRID 1588955노트

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HRID 1588955 반응식
[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C[O:18][C:19](=[O:24])/[CH:20]=[CH:21]/CBr.O.[C:26](O)(=O)C>[Zn].II.CCOCC>[C:1]([O:5][C:6]([C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:15])([CH3:26])[CH2:14][CH:21]=[CH:20][C:19]([OH:24])=[O:18])=[CH:11][CH:12]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 53691752-Butenoic acid, 4-bromo-, methyl ester2회HCID 13844704tert-Butyl 4-acetylbenzoate

생성물 1

HCID 54165322HCID 54165322, 화합물

시약·촉매·용매 3

HCID 807Iodine촉매HCID 23994Zinc촉매2회HCID 3283Diethyl Ether용매

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온도
70 °C

실험 절차

To a suspension obtained by adding a solution of 4-acetylbenzoic acid tert-butyl ester (7.82 g) in benzene-ether-tetrahydrofuran (3:3:2, 80 ml) to 4.64 g (71 mmol) of zinc, were added gradually under heating and stirring 4-bromocrotonic acid methyl ester (6.36 g) and iodine (20 mg). After reflux under heating in an oil bath at 70° C. for 1 hour, methyl 4-bromocrotonate (2.13 g) and zinc (1.55 g) were added, followed by reflux under heating for 30 minutes. The temperature was cooled down to room temperature, and the reaction mixture was poured into water (300 ml) and adjusted to pH 5 with acetic acid. The organic layer obtained by extraction with ether was washed with 5% aqueous ammonia and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by column chromatography (support; silica gel, 200 g, developing agent; ethyl acetate:hexane=1:4), to obtain the object compound (9.2 g).

후처리

  1. customTo a suspension obtained
  2. additionwere added gradually
  3. temperatureunder heating
  4. temperatureAfter reflux
  5. temperatureby reflux
  6. temperatureunder heating for 30 minutes
  7. temperatureThe temperature was cooled down to room temperature
  8. washwas washed with 5% aqueous ammonia
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe resulting residue was purified by column chromatography (support; silica gel, 200 g, developing agent; ethyl acetate:hexane=1:4)

출처 및 근거

ORD 기록
ord-c6577c445ec5422a99e5271beda5fb80
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223620

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