Hydrogen Bromide → 7-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

HRID 65012

Reaktionsgleichung

Reaktionsgleichung von HRID 65012
C[O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH:8]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])([CH3:13])[CH:8]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 141266497-Methoxy-3-piperidino-2,2-dimethylbenzofuran

Produkt 1

HCID 141266507-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

7-Methoxy-3-piperidino-2,2-dimethylbenzofuran (65.1 g) is added to a stirred mixture of glacial acetic acid (340 ml) and 48% HBr (340 ml) and the solution refluxed for 3 hours. The reaction mixture is poured into crushed ice/H2O and brought to a pH=8-10. The alkaline reaction mixture is extracted with methylene chloride and the organic phase washed with water, dried, filtered and evaporated in vacuo. The residue is chromatographed on silica gel eluting with ethyl acetate/hexane (1:3) affording the desired product as a liquid.

Aufarbeitung

  1. temperaturethe solution refluxed for 3 hours
  2. additionThe reaction mixture is poured
  3. customThe alkaline reaction mixture
  4. extractionis extracted with methylene chloride
  5. washthe organic phase washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue is chromatographed on silica gel eluting with ethyl acetate/hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-347dde3bfff44297b7d1855c4755765d
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612309

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