Cyclohexanone → HCID 10541879, compound

HRID 1408803Notes

Reaction equation

HRID 1408803 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.N1CCCC1.[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:17]1([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 10541879HCID 10541879, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (60 g, 280 mmol) and pyrrolidine (37.8 g, 532 mmol) in methanol (1200 mL) was added cyclohexanone (55 g, 560 mmol), and the mixture was reflux overnight. The solvent was removed in vacuo, and then added H2O and HCl to make the mixture to PH=1, extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromospiro[chroman-2,1′-cyclohexan]-4-one (90 g, 100%). 1H NMR (CDCl3): 1.49 (d, 4H), 1.64 (d, 4H), 1.83 (s, 1H), 1.98 (d, 2H), 2.11 (t, 1H), 2.31 (s, 1H), 2.68 (s, 1H), 6.87 (d, 1H), 7.50 (d, 1H), 7.92 (s, 1H).

Workup

  1. temperaturethe mixture was reflux overnight
  2. customThe solvent was removed in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e8f4dc64790e49058cf1bb615eff4ba9
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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