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Potassium Carbonate → Methyl 4-((4E)-5-{2-[(4-tert-butylbenzyl)oxy]phenyl}-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-ethyl}pent-4-en-1-yl)benzoate

HRID 1920580
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HRID 1920580 반응식
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:21][C:22](=[O:51])[CH2:23][C:24]1([CH2:27][CH2:28][CH:29](/[CH:42]=[CH:43]/[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[OH:50])[CH2:30][CH2:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)[CH2:26][CH2:25]1)[CH3:20]>C(#N)C>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:50][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2/[CH:43]=[CH:42]/[CH:29]([CH2:28][CH2:27][C:24]2([CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:51])[CH2:25][CH2:26]2)[CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:40][CH:41]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57965770Methyl 4-[(4E)-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate

생성물 1

HCID 57965760Methyl 4-((4E)-5-{2-[(4-tert-butylbenzyl)oxy]phenyl}-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-ethyl}pent-4-en-1-yl)benzoate

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

134.6 mg (0.59 mmol) of 4-(tert-butyl)benzyl bromide and 163.8 mg (1.18 mmol) of anhydrous potassium carbonate are added to a solution of 178 mg (0.395 mmol) of methyl 4-[(4E)-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate in 5 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). This gives 130.6 mg (55% of theory) of a solid.

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated

출처 및 근거

ORD 기록
ord-223901bad6a7488cbe691d428666bd0f
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08168821B2

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