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

HRID 1698738

반응식

HRID 1698738 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dc6960bf1c9e4c31abc9c0b7d433fc03
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163787B2

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