Dimethylformamide → 4-(3-Hydroxypropyloxy)-chalcone

HRID 2298728

Reaktionsgleichung

Reaktionsgleichung von HRID 2298728
CN([CH:4]=[O:5])C.O[C:7]1[CH:22]=[CH:21][C:10]([C:11](=[O:20])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.[H-].[Na+].ClC[CH2:27][CH2:28][OH:29]>O>[OH:29][CH2:28][CH2:27][CH2:4][O:5][C:17]1[CH:18]=[CH:19][C:14]([CH:13]=[CH:12][C:11]([C:10]2[CH:21]=[CH:22][CH:7]=[CH:8][CH:9]=2)=[O:20])=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 123133-Chloro-1-propanolHCID 24758Sodium hydrideHCID 942401-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one

Produkt 1

HCID 684721924-(3-Hydroxypropyloxy)-chalcone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A refined 4′-(3-hydroxypropyloxy)-chalcone (9.71 g, 34.4 mmol) was obtained with a yield of 51.4% by adding 90 ml of dry DMF to 4′-hydroxychalcone (15.0 g, 67 mmol) in an air current of argon, and adding sodium hydride (60%, 2.68 g, 67 mmol) through dropping in a reaction flask of 200 ml in ice cooling for 30 minutes; later, after heating to a room temperature and stirring for 5 hours, adding 3-chloro-1-propanol (6.33 g, 67 mmol) through dropping at the same temperature for 10 minutes; furthermore, heating to 80° C., and reacting for 7 hours; next, after injecting the solution into water with ice and extracting the product with ethyl acetate, washing with water, and drying through dehydration with magnesium sulfate, and removing the solvent; after refining (mobile phase, hexane:ethyl acetate=4:1) the gained coarse crystal with silica gel column, recrystallizing with ethyl acetate.

Aufarbeitung

  1. waitthrough dropping at the same temperature for 10 minutes
  2. temperaturefurthermore, heating to 80° C.
  3. waitreacting for 7 hours
  4. extractionextracting the product with ethyl acetate
  5. washwashing with water
  6. dry with materialdrying through dehydration with magnesium sulfate
  7. customremoving the solvent
  8. customrecrystallizing with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6313d0c580d9494795cb6dc933f0fa1b
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495221B1

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