Diethyl Ether → 5-(alpha-Hydroxyundecyl)-3-phenylbenzofuran

HRID 262217

Reaktionsgleichung

Reaktionsgleichung von HRID 262217
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1.[Mg].[Cl-].[NH4+].C([O:22][CH2:23][CH3:24])C>O1CCCC1.O>[OH:22][CH:23]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1)[CH2:24][CH2:4][CH2:3][CH2:2][CH2:16][CH2:6][CH2:7][CH2:10][CH2:11][CH3:12]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 203301645-Bromo-3-phenyl-1-benzofuran

Produkt 1

HCID 213202985-(alpha-Hydroxyundecyl)-3-phenylbenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5.5 g. (0.02 mole) of 5-bromo-3-phenylbenzofuran in tetrahydrofuran is added 0.5 g. (0.02 mole) of magnesium, and the mixture is heated at its reflux temperature for three hours. After cooling to 0° C., 3.4 g. of undecyl aldehyde is added. After stirring for 30 minutes at room temperature, the solution is added to ammonium chloride solution. Evaporation provides a residue which is mixed with diethyl ether and water. The ether layer is separated, washed with saturated sodium chloride solution, dried and evaporated. The resulting oil is dissolved in carbon tetrachloride and eluted from a silica gel column with carbon tetrachloride, then with dichloromethane. The later fractions are evaporated to provide 5-(α-hydroxyundecyl)-3-phenylbenzofuran which is dissolved in dichloromethane.

Aufarbeitung

  1. temperaturereflux temperature for three hours
  2. customEvaporation
  3. customprovides a residue which
  4. customThe ether layer is separated
  5. washwashed with saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. dissolutionThe resulting oil is dissolved in carbon tetrachloride
  9. washeluted from a silica gel column with carbon tetrachloride
  10. customThe later fractions are evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c49d250a9e154af5b535095b9dcf3100
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04153716

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