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Potassium Carbonate → 6-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde

HRID 445225
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HRID 445225 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]=1[CH:14]=[O:15].[N:16]1([CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([O:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:26][CH:27]=1)=[C:3]([CH:14]=[O:15])[CH2:4][CH2:5]2
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 106090214-[2-(Piperidin-1-yl)ethoxy]phenolHCID 112530501-Chloro-6-methoxy-3,4-dihydronaphthalene-2-carbaldehyde

생성물 1

HCID 583385916-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde수율 122.4%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine
촉매

반응 조건

온도
100 °C

실험 절차

To a 3-necked round bottom flask, add 1-chloro-6-methoxy-3,4-dihydronaphthalene-2-carbaldehyde (2.25 g, 10.1 mmol), 4-(2-(piperidin-1-yl)ethoxy)phenol (1.8 g, 8.24 mmol), tetra-N-butylammonium iodide (50 mg, 0.14 mmol), potassium carbonate (4.1 g, 29.8 mmol), and 4-dimethylaminopyridine (120 mg, 0.99 mmol). Purge the reaction vessel with nitrogen. Add dimethylformamide (30 mL) slowly to the reaction. Heat the mixture to 100° C. with stirring and hold for 4 hours. Cool the reaction mixture to room temperature and quench with ice-water. Extract the mixture with ethyl acetate three times. Dry the combined organic layers over MgSO4, filter, and concentrate to give 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde (4.11 g).

후처리

  1. customPurge the reaction vessel with nitrogen
  2. customAdd dimethylformamide (30 mL) slowly to the reaction
  3. temperatureCool the reaction mixture to room temperature
  4. customquench with ice-water
  5. extractionExtract the mixture with ethyl acetate three times
  6. dry with materialDry the combined organic layers over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate

출처 및 근거

ORD 기록
ord-665326ce43e44f6d9c6e57583f565fd5
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08476300B2

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