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

HRID 259389

Reaction equation

HRID 259389 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 11/2 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.

Workup

  1. customis decanted from excess metal
  2. custom2 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.

Sources & evidence

ORD record
ord-ecfd5e6d54e74309bff4d1113272e89d
Source dataset
uspto-grants-1977_07
Patent number
US04038273

Linked notes

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