Hydrochloric Acid → HCID 22123586, Verbindung

HRID 1859333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859333
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:32])[C:13]3[CH:14]=[CH:15][C:16]([O:18][CH2:19][O:20][CH3:21])=[CH:17][C:12]=3[O:11][CH2:10][CH:9]2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.Cl[CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.Cl.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[OH:32][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:3][CH:4]=2)[C:13]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][O:20][CH3:21])=[CH:17][C:12]=2[O:11][CH2:10][CH:9]1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 220333324-Hydroxy-4-(4-hydroxyphenyl)-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman

Produkt 1

HCID 22123586HCID 22123586, VerbindungAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-(4-Hydroxyphenyl)-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran (310 mg, 0.59 mmol) prepared in Example 15, [1-(2-chloroethyl)]piperidine.HCl (176 mg, 0.9 mmol) and K2CO3 (264 mg, 1.8 mmol) were dissolved in acetone (8 ml) and then refluxed for 62 hours. The reaction solution was cooled to room temperature and, after adding water, extracted with ethyl acetate. The organic layer thus separated was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to remove the organic solvent. The residue was separated by column chromatography (n-hexane:ethyl acetate=1:2) to obtain 83 mg (yield: 7%) of the title compound as a white foam.

Aufarbeitung

  1. temperaturerefluxed for 62 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer thus separated
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto remove the organic solvent
  8. customThe residue was separated by column chromatography (n-hexane:ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-5340d8aba9514215a5d6fffe273938b8
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153768

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