Sulfuric Acid → ethyl 10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene-2-carboxylate

HRID 885419노트

반응식

HRID 885419 반응식
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]1=2.C(OCC)(OCC)O[CH2:22][CH3:23].S(=O)(=O)(O)O>C(O)C.C(OCC)(=O)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH2:22][CH3:23])=[O:14])=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]1=2

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 31214Ethyl orthoformateHCID 125258755-Oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-2-carboxylic acid

생성물 1

HCID 67211051ethyl 10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene-2-carboxylate수율 94%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

[step 1] 5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-2-carboxylic acid (JP-B-2526005, 19.9 g, 79 mmol) and triethyl orthoformate (17.0 mL, 102 mmol) were dissolved in ethanol (130 mL), followed by adding concentrated sulfuric acid (1.68 mL, 32 mmol) and the mixture was stirred under reflux for 12 hr. The mixture was diluted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10) to give ethyl 5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-2-carboxylate (20.8 g, 94%).

후처리

  1. temperatureunder reflux for 12 hr
  2. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10)

출처 및 근거

ORD 기록
ord-f0290d29aef146bb918f6953f59f159c
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242151B2

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