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

HRID 885419ノート

反応式

HRID 885419 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

[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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f0290d29aef146bb918f6953f59f159c
出典データセット
uspto-grants-2012_08
特許番号
US08242151B2

反応ノート

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