Pyrrolidine → 6-Bromo-3',5'-dimethylspiro[chroman-2,1'-cyclohexan]-4-one

HRID 2096499Notes

Reaction equation

HRID 2096499 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.[CH3:12][CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16][C:15](=O)[CH2:14]1.N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:15]1([CH2:16][CH:17]([CH3:19])[CH2:18][CH:13]([CH3:12])[CH2:14]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 1375443,5-Dimethylcyclohexanone

Product 1

HCID 584244886-Bromo-3',5'-dimethylspiro[chroman-2,1'-cyclohexan]-4-oneYield 110.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (6 g, 28 mmol), 3,5-dimethylcyclohexanone (7.12 g, 56 mmol) and pyrrolidine (3.8 g, 53.3 mmol) in methanol (120 mL) was stirred overnight. The reaction mixture was concentrated in vacuo, and H2O was added. The resulting solution was extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 6-bromo-3′,5′-dimethylspiro[chroman-2,1′-cyclohexan]-4-one (10 g, 100%). 1HNMR (CDCl3): 0.51 (m, 1H), 0.71 (m, 4H), 0.72 (m, 3H), 0.91 (m, 3H), 1.11 (d, 1H), 1.19 (t, 1H), 1.50 (s, 1H), 1.64 (t, 1H), 1.79 (m, 3H), 1.90 (m, 2H), 2.0 (m, 3H), 2.24 (t, 1H), 2.53 (s, 1H), 2.79 (s, 1H), 6.75 (t, 1H), 7.49 (t, 1H), 7.89 (d, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, and H2O
  2. additionwas added
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97eab8273529427089635ca5ae77490b
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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