Tetrahydrofuran → 1-(t-Butoxycarbonylmethoxyphenyl)-3,5-di(4-hydroxyphenyl)benzene

HRID 1618854

Reaktionsgleichung

Reaktionsgleichung von HRID 1618854
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:28][C:29]([CH3:32])([O-:31])[CH3:30].[K+].Br[CH:35](C(C)(C)C)[C:36]([O-:38])=O.[O:43]1CCCC1>>[C:29]([O:31][C:35]([CH2:36][O:38][C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH:11]=[C:10]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH:9]=1)=[O:43])([CH3:32])([CH3:30])[CH3:28]

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 3481481,3,5-Tris(4-hydroxyphenyl)benzeneHCID 21584499Bromo-t-butylacetateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 688621581-(t-Butoxycarbonylmethoxyphenyl)-3,5-di(4-hydroxyphenyl)benzene

Versuchsvorschrift

18 g of 1,3,5-tris(4-hydroxyphenyl)benzene was dissolved in 500 ml of tetrahydrofuran. 6 g of potassium t-butoxide was added and the mixture was stirred at room temperature for five minutes. After the addition of 10 g of bromo-t-butylacetate dropwise, the mixture was stirred for six hours while heating at 60° C. After evaporating tetrahydrofuran under reduced-pressure, the reaction product was extracted with 300 ml of dichloromethane, purified using a silica gel column, and dried to obtain 4.6 g of 1-(t-butoxycarbonylmethoxyphenyl)-3,5-di(4-hydroxyphenyl)benzene.

Aufarbeitung

  1. stirringthe mixture was stirred for six hours
  2. temperaturewhile heating at 60° C
  3. customAfter evaporating tetrahydrofuran under reduced-pressure
  4. extractionthe reaction product was extracted with 300 ml of dichloromethane
  5. custompurified
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bc4d19b534eb4a389ecc6e4921082874
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08771923B2

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