N-Formylmorpholine → 4-Methoxy-8,9-dihydro-5,7-dioxabenzocycloheptene-2-carbaldehyde

HRID 1698738

反応式

HRID 1698738 の反応式
Br[C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]2[O:11][CH2:10][O:9][CH2:8][CH2:7][C:6]=2[CH:12]=1.C([Li])CCC.[CH:20](N1CCOCC1)=[O:21].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH3:14][O:13][C:4]1[C:5]2[O:11][CH2:10][O:9][CH2:8][CH2:7][C:6]=2[CH:12]=[C:2]([CH:20]=[O:21])[CH:3]=1

参加物

7

反応物 4

HCID 20417N-FormylmorpholineHCID 25517Ammonium ChlorideHCID 595172132-Bromo-4-methoxy-8,9-dihydro-5,7-dioxabenzocyclohepteneHCID 178418339Butyllithium

生成物 1

HCID 595170474-Methoxy-8,9-dihydro-5,7-dioxabenzocycloheptene-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-70 °C

実験手順

To a solution of 420 mg of 2-bromo-4-methoxy-8,9-dihydro-5,7-dioxa-benzocycloheptene in 10 ml of THF there was added dropwise 0.7 ml of n-butyllithium (2.66 M, hexane solution) at −70° C. under a nitrogen atmosphere. After stirring at −70° C. for 10 minutes, 0.5 ml of N-formylmorpholine was added and the temperature was raised from −70° C. to 0° C. over a period of 30 minutes. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (235 mg) as an oil.

後処理

  1. temperaturethe temperature was raised from −70° C. to 0° C. over a period of 30 minutes
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

出典と根拠

ORDレコード
ord-dc6960bf1c9e4c31abc9c0b7d433fc03
出典データセット
uspto-grants-2012_04
特許番号
US08163787B2

関連ノート

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