beta-Bromostyrene → 1-Methyl-2-styryl-2-hydroxy-6-piperidone

HRID 1658292

Reaktionsgleichung

Reaktionsgleichung von HRID 1658292
[Mg].Br[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][N:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=[O:19].[NH4+].[Cl-]>C1COCC1>[CH3:11][N:12]1[C:13](=[O:19])[CH2:14][CH2:15][CH2:16][C:17]1([CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:18]

Komponenten

6

Edukt 4

HCID 7667beta-BromostyreneHCID 25517Ammonium ChlorideHCID 1614762,6-Piperidinedione, 1-methyl-HCID 5462224Magnesium

Produkt 1

HCID 537761611-Methyl-2-styryl-2-hydroxy-6-piperidone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The Grignard reagent prepared in 300 ml of THF from 24 g (1.0 mole) of magnesium and 42 g (0.30 mole) of β-bromostyrene is decanted from excess metal and added dropwise under nitrogen to a solution of 27 g (0.21 moles) of N-methyl glutarimide at 3°-5°. After 1 1/2 hrs. at room temperature, the mixture is treated with 250 ml of saturated NH4Cl solution with cooling. The separated aqueous layer is reextracted and the combined THF extracts washed with salt, dried over MgSO4 and freed of solvent. Product is extracted into hot ether and crystallized on cooling to yield white crystals, mp 108°-112°C.

Aufarbeitung

  1. customis decanted from excess metal
  2. customAfter 1 1/2 hrs
  3. temperaturewith cooling
  4. washthe combined THF extracts washed with salt
  5. dry with materialdried over MgSO4
  6. extractionProduct is extracted into hot ether
  7. customcrystallized
  8. temperatureon cooling
  9. customto yield white crystals, mp 108°-112°C.

Quellen und Nachweise

ORD-Eintrag
ord-51104cfd4e584a33ba824d08349edf7b
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03963724

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