Resorcinol → 6-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carboxylic acid

HRID 445226노트

반응식

HRID 445226 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8]([CH:29]=[O:30])[CH2:7][CH2:6]2.C1(C=CC=C(O)C=1)[OH:32].C1COCC1.Cl([O-])=O.[Na+]>O.C(O)(=O)C.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:16][CH:15]=1)=[C:8]([C:29]([OH:32])=[O:30])[CH2:7][CH2:6]2

참가 물질

8

반응물 4

HCID 5054ResorcinolHCID 8028TetrahydrofuranHCID 23668197Sodium ChloriteHCID 583385916-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde

생성물 1

HCID 583385566-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carboxylic acid수율 21.8%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

To a round bottom flask, add 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde (3.0 g, 4.34 mmol), resorcinol (531 mg, 4.8 mmol), THF (8 mL), ethanol (8 mL) and acetic acid (0.9 mL). Stir the mixture at 25° C. for 5 min. Add slowly sodium chlorite (1.3 g, 11.2 mmol) in water (8 mL) to the reaction mixture. Stir the mixture at 80° C. for 2 hours. Quench the reaction mixture with ice-water. Add ethyl acetate to the vessel with stirring. Wash the mixture with dilute NaOH three times and discard the organic phase. To the aqueous layer, add water so the pH was adjusted to 5-6. Extract the aqueous layer with ethyl acetate five times and discard the aqueous phase. Dry the organic layer over MgSO4, filter, and concentrate to dryness, which was further purified to give 400 mg of 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carboxylic acid. 1HNMR (d-DMSO, 300 MHZ): 9.97 (1H, s) 7.12 (1H, m), 6.86 (5H, m), 6.71 (1H, m), 4.27 (2H, m), 3.73 (3H, s), 4.26 (2H, s), 3.41 (3H, m), 2.82 (2H, m), 2.59 (2H, m), 1.70 (6H, m).

후처리

  1. stirringStir the mixture at 80° C. for 2 hours
  2. customQuench the reaction mixture with ice-water
  3. stirringAdd ethyl acetate to the vessel with stirring
  4. washWash the mixture with dilute NaOH three times
  5. additionTo the aqueous layer, add water so the pH
  6. extractionExtract the aqueous layer with ethyl acetate five times
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate to dryness, which
  10. customwas further purified

출처 및 근거

ORD 기록
ord-7da1ce96bfd04a149dcfedb0eef1113a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476300B2

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