Pyridine → 2,4,4'-Trihydroxydeoxybenzoin

HRID 1760763

Reaktionsgleichung

Reaktionsgleichung von HRID 1760763
FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1.[OH:20][C:21]1(C(F)(F)F)[C:26]2[CH:27]=[CH:28][C:29]([OH:31])=[CH:30][C:25]=2[O:24]C(C2C=CC(OCCN3CCCCC3)=CC=2)[CH:22]1[C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:24][C:25]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:26]=1[C:21](=[O:20])[CH2:22][C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 155474944,7-dihydroxy-3-(4-hydroxyphenyl)-2-[4-(2-piperidin-1-ylethoxy)-phenyl]-4-(trifluoromethyl)-2,3-dihydro-4H-1-benzopyran

Produkt 1

HCID 6400962,4,4'-Trihydroxydeoxybenzoin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.88 ml of trifluoroacetic acid anhydride and 1.37 ml of pyridine are simultaneously added in drops to 1.15 g of 4,7-dihydroxy-3-(4-hydroxyphenyl)-2-[4-(2-piperidin-1-ylethoxy) -phenyl]-4-(trifluoromethyl)-2,3-dihydro-4H-1-benzopyran in 20 ml of THF. It is stirred for 4 hours at room temperature before 70 ml of ethyl acetate and 20 ml of 10% sodium carbonate solution are added. It is stirred for 20 more minutes at room temperature. The phases are separated, and the aqueous phase is shaken out three times with 40 ml of ethyl acetate. The combined organic phases are washed twice with 20 ml of water, dried on magnesium sulfate and concentrated by evaporation. The product is prepurified on silica gel with dichloromethane/methanol and then purified with HPLC (nucleosil 50-7, dichloromethane/methanol 85:15, 40 ml/min). 590 mg is obtained.

Aufarbeitung

  1. additionare added
  2. customThe phases are separated
  3. stirringthe aqueous phase is shaken out three times with 40 ml of ethyl acetate
  4. washThe combined organic phases are washed twice with 20 ml of water
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. custompurified with HPLC (nucleosil 50-7, dichloromethane/methanol 85:15, 40 ml/min)
  8. custom590 mg is obtained

Quellen und Nachweise

ORD-Eintrag
ord-f1614aa6f5ea4a6ea4c7928fb712567a
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844336B2

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